Preparing Primary Amines Patents (Class 564/407)
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Patent number: 11981616Abstract: A method for preparing 3,3?-diaminobenzidine, the method comprising the following steps: subjecting 4,4?-biphenol and N,N-dimethylsulfamoyl chloride to an esterification reaction in a specified solvent at 40-70° C. to obtain 4,4?-biphenyl bis(N,N-dimethylaminosulfonate) as a first intermediate; subjecting the 4,4?-biphenyl bis(N,N-dimethylaminosulfonate) to a chlorination reaction with a chlorinating reagent under acidic conditions to obtain 3,3?-dichloro-4,4?-biphenyl bis(N,N-dimethylaminosulfonate) as a second intermediate; subjecting the second intermediate 3,3?-dichloro-4,4?-biphenyl bis(N,N-dimethylaminosulfonate) to an ammonolysis reaction with anammoniation reagent in the presence of a combined catalyst to obtain a crude product of 3,3?,4,4?-tetraaminobiphenyl, wherein the combined catalyst is a mixture of proline, a cuprous salt and a phase transfer catalyst; and subjecting the crude product of 3,3?,4,4?-tetraaminobiphenyl to a post-treatment to obtain a purified 3,3?,4,4?-tetraaminobiphenyl product.Type: GrantFiled: January 12, 2022Date of Patent: May 14, 2024Assignees: Hubei Huida High-Tech Co., Ltd, Borun High-Tech Co., Ltd.Inventors: Yun Ling, Yongfang Li, Kun Wang, Lizhu Chen, Wei Yin, Jinying Zhang
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Patent number: 11453670Abstract: The present invention provides improved methods for the preparation of substituted heterocycle fused gamma-carbolines, intermediates useful in producing them and methods for producing such intermediates and such heterocycle fused gamma-carbolines.Type: GrantFiled: August 16, 2019Date of Patent: September 27, 2022Assignee: INTRA-CELLULAR THERAPIES, INC.Inventors: Peng Li, Qiang Zhang
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Patent number: 8766008Abstract: Process for preparing 2,2-difluoroethylamine, comprising the following steps: (i) mixing 2,2-difluoro-1-chloroethane and gaseous, liquid or supercritical ammonia in a pressure-stable, closed reaction vessel under a pressure in the range from 10 to 180 bar; (ii) reacting the reaction mixture at a reaction temperature in the range from 80° C. to 200° C.; (iii) letting down the reaction mixture and isolating 2,2-difluoroethylamine.Type: GrantFiled: January 11, 2012Date of Patent: July 1, 2014Assignee: Bayer Cropscience AGInventors: Norbert Lui, Rafael Warsitz, Christian Funke, Christian Severins
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Patent number: 8426646Abstract: The present invention relates to a process for the preparation of compounds of formula (I) wherein R1 is C6-C7 alkyl or a group (A1) wherein R2, R3 and R4 are each independently of the others hydrogen or C1-C4 alkyl; wherein a compound of formula (II) wherein R1 is as defined for formula (I) and X is bromine or chlorine, is reacted with urea in the presence of a base and a catalytic amount of at least one palladium complex compound, wherein the palladium complex compound comprises at least one ferrocenyl-biphosphine ligand.Type: GrantFiled: June 30, 2008Date of Patent: April 23, 2013Assignee: Syngenta Crop Protection LLCInventors: Maren Fuerst, Thomas Vettiger
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Patent number: 8058477Abstract: A catalytic process for the synthesis of aromatic primary amines, reagent compositions for effecting the process, and transition metal complexes useful in the process, are provided.Type: GrantFiled: March 20, 2007Date of Patent: November 15, 2011Assignee: Yale UniversityInventors: John F. Hartwig, Qilong Shen
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Publication number: 20100298571Abstract: The invention relates to a method for preparing arylamines and, in particular, a method for preparing aniline and anilines substituted on the aromatic ring from ammonia, under easily-industrialised mild conditions with good selectivity and yields, in the presence of a catalytic system including a copper complex.Type: ApplicationFiled: September 24, 2008Publication date: November 25, 2010Inventors: Marc Taillefer, Ning Xia
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Publication number: 20100256417Abstract: The present invention relates to a process for the preparation of compounds of Formula (I), wherein R1 is 1,3-dimethyl-butyl, 1,3,3-trimethyl-butyl or a group A1, wherein R3, R4 and R5 are each independently of the others hydrogen or C1-C4alkyl; and R2 is hydrogen; or R1 and R2 together from the group A2, wherein R6, and R7 are each independently of the other hydrogen or C1-C4alkyl; or R1 and R2 together from the group A3, wherein R5 and R9 are each independently of the other hydrogen or C1-C4alkyl; wherein a compound of Formula (II) wherein R1 and R2 are as defined for formula I and X is bromine or chlorine, is reacted with ammonia in the presence of a base and a catalytic amount of at least one palladium complex compound, wherein the palladium complex compound comprises at least one ferrocenyl-biphosphine ligand.Type: ApplicationFiled: August 6, 2007Publication date: October 7, 2010Applicant: SYNGENTA CROP PROTECTION, INC.Inventors: Harald Walter, Ulrike Nettekoven
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Publication number: 20100228055Abstract: The present invention relates to a process for the preparation of compounds of formula (I) wherein R1 is C6-C7 alkyl or a group (A1) wherein R2, R3 and R4 are each independently of the others hydrogen or C1-C4 alkyl; wherein a compound of formula (II) wherein R1 is as defined for formula (I) and X is bromine or chlorine, is reacted with urea in the presence of a base and a catalytic amount of at least one palladium complex compound, wherein the palladium complex compound comprises at least one ferrocenyl-biphosphine ligand.Type: ApplicationFiled: June 30, 2008Publication date: September 9, 2010Applicant: SYNGENTA CROP PROTECTION, INC.Inventors: Maren Fuerst, Thomas Vettiger
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Patent number: 7781615Abstract: The present invention relates to a novel a process for the preparation of the compound of the general formula (I), wherein R1 and R2 are independently H or C1-6 alkyl, which comprises treating with a reducing agent either a compound of the general formula (II), wherein R1 and R2 have the meanings given for the compound of the formula (I), R3 is H or C1-4alkyl and Ph is phenyl, or a compound of the general formula (III), wherein R1, R2, R3 and Ph have the meanings given for the compound of the formula (II), the reducing agent being effective to cleave the benzyl moiety Ph-CH(R3)— from the benzylamino moiety PhCH(R3)NH— in the compound of the formula (II) or in the compound of the formula (III) to leave an amino group and, in addition, in the case of the compound of the formula (III), to reduce both the 2,3-double bond and the double bond joining the R1R2C— moiety to the 9-position of the benzonorbornene ring to single bonds.Type: GrantFiled: December 11, 2006Date of Patent: August 24, 2010Assignee: Syngenta Crop Protection, Inc.Inventors: Hans Tobler, Harald Walter, Camilla Corsi, Josef Ehrenfreund, Fanny Giordano, Martin Zeller
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Patent number: 7777079Abstract: This invention is involved with a preparation method of 2,6-dichloro-4-trifluoromethyl-aniline. With this process, p-Chlorobenzotrifluoride is used as the starting material and subjected to halogenation reaction and ammoniation reaction and through separation of reaction products the desired 2,6-dichloro-4-trifluoromethyl-aniline is obtained. In addition, ammonia is recovered from the surplus ammonia water in ammoniation reaction. This applied invention in characterized by simple process, cheap and easy-available raw materials, high reaction yield and friendly environment.Type: GrantFiled: March 23, 2009Date of Patent: August 17, 2010Assignee: Zhejiang Weihua Chemical Co., Ltd.Inventors: Huiyue Li, Jinghua Chen, Jiangwei Wu, Guirong Huang, Xinping Zhao, Kaiquan Wang
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Patent number: 7767856Abstract: Improved methods for making hole transport molecules (HTMs) that are incorporated into imaging members, such as layered photoreceptor devices, to increase the photoreceptor's “hole mobility,” or its ability to move charge, across its charge transport layer (CTL). Embodiments pertain to a continuous process for making N,N-diphenyl-4-biphenylamine and a system for performing the same.Type: GrantFiled: January 25, 2007Date of Patent: August 3, 2010Assignee: Xerox CorporationInventors: Timothy P. Bender, Emily L. Moore, Jennifer A. Coggan, Frank Ping-Hay Lee, David Borbely
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Publication number: 20090240083Abstract: This invention is involved with a preparation method of 2,6-dichlor-4-trifluoromethyl aniline. With this process, 4-chlorotrifluoromethyl benzene is used as the starting material and subjected to halogenation reaction and ammoniation reaction and through separation of reaction products the desired 2,6-dichlor-4-trifluoromethyl aniline is obtained. In addition, ammonia is recovered from the surplus ammonia water in ammoniation reaction. This applied invention in characterized by simple process, cheap and easy-available raw materials, high reaction yield and friendly environment.Type: ApplicationFiled: March 23, 2009Publication date: September 24, 2009Applicant: Zhejiang Weihua Chemical Co., Ltd.Inventors: Huiyue Li, Jinghua Chen, Jiangwei Wu, Guirong Huang, Xinping Zhao, Kaiquan Wang
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Publication number: 20090234126Abstract: A catalytic process for the synthesis of aromatic primary amines, reagent compositions for effecting the process, and transition metal complexes useful in the process, are provided.Type: ApplicationFiled: March 20, 2007Publication date: September 17, 2009Applicant: YALE UNIVERSITYInventors: John F. Hartwig, Qilong Shen
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Publication number: 20090177011Abstract: The present invention relates to a process for the preparation of compounds of formula (I) wherein R1, R2 and R3 are each independently of the others hydrogen or methyl, by reaction of compounds of formula (II) wherein R1, R2 and R3 are as defined for formula (I) and X is bromine or chlorine, with ammonia in the presence of a catalytic amount of at least one copper-containing compound.Type: ApplicationFiled: December 8, 2005Publication date: July 9, 2009Applicant: Syngenta Crop Protection, Inc.Inventors: Harald Walter, Camilla Corsi, Josef Ehrenfreund, Clemens Lamberth, Hans Tobler
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Patent number: 7408085Abstract: A process for forming a tetra(aryl)-biphenyldiamine compound, including reacting a dibromobiphenyl compound and a diarylamine compound in the presence of a palladium ligated catalyst and a base.Type: GrantFiled: November 28, 2006Date of Patent: August 5, 2008Assignee: Xerox CorporationInventors: Timothy P. Bender, Jennifer A. Coggan, Gregory McGuire, Leanne Dawn Murphy, Alan Edward John Toth
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Patent number: 7402700Abstract: A process for forming a diarylamine compound, including reacting an aniline and an arylbromide in the presence of a palladium ligated catalyst and a base.Type: GrantFiled: November 28, 2006Date of Patent: July 22, 2008Assignee: Xerox CorporationInventors: Timothy P. Bender, Jennifer A. Coggan
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Patent number: 7345203Abstract: A process for forming a triarylamine compound, including reacting an aniline and an arylchloride in the presence of a ligated palladium catalyst and a base.Type: GrantFiled: November 28, 2006Date of Patent: March 18, 2008Assignee: Xerox CorporationInventors: Timothy P. Bender, Jennifer A. Coggan
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Patent number: 7321066Abstract: The invention provides a method for efficiently producing an aromatic diamine derivative represented by formula (3) at high yield, the method including reacting an aromatic amide represented by formula (1) with an aromatic halide represented by formula (2): (wherein each of Ar, Ar1 and Ar2 represents a substituted or unsubstituted aryl group or heteroaryl group; Ar3 represents a substituted or unsubstituted arylene group or heteroarylene group; and X represents a halogen atom).Type: GrantFiled: January 28, 2004Date of Patent: January 22, 2008Assignee: Idemitsu Kosan Co., Ltd.Inventors: Hisayuki Kawamura, Hiroyuki Matsui, Koji Hirota
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Patent number: 6759554Abstract: The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate.Type: GrantFiled: April 24, 2002Date of Patent: July 6, 2004Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Artis Klapars, Jon C. Antilla, Gabriel E. Job, Martina Wolter, Fuk Y. Kwong, Gero Nordmann, Edward J. Hennessy
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Publication number: 20030083525Abstract: The present invention describes a process for preparing 4-amino-1-naphthol ethers which is characterized in that naphthol ethers are first prepared from 1-naphthols, the former are then converted to the corresponding 4-acetamino-1-naphthol ethers and then the acyl group is cleaved off, and further describes 4-acetamino-1-naphthol ethers obtained thereby.Type: ApplicationFiled: August 27, 2002Publication date: May 1, 2003Inventors: Joachim Komoschinski, Herbert Diehl
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Patent number: 6538158Abstract: 1,4-diaminonaphthalene and/or 1,5-diaminonaphthalene are produced by (a) reacting naphthalene with a halogen, (b) optionally, separating 1,4-dihalogen naphthalene or 1,5-dihalogen naphthalene from the mixture from step (a), and (c) reacting the mixture from step (a) or the 1,4-dihalogen naphthalene or the 1,5-dihalogen naphthalene from step (b) with ammonia and/or an organic amine in the presence of a catalyst.Type: GrantFiled: May 3, 2002Date of Patent: March 25, 2003Assignee: Bayer AktiengesellschaftInventors: Joachim Zechlin, Lothar Duda, Gerhard Wegener, Andreas Hoffmann, Bodo Temme
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Patent number: 6476265Abstract: In a process for preparing aryl oligoamines, an amine is reacted with an activated aromatic and a base in a temperature range from 0 to 150° C. in the presence of a palladium component and a phosphine ligand. The aryl oligoamines are obtained simply and in good yields.Type: GrantFiled: May 10, 2000Date of Patent: November 5, 2002Assignee: Covion Organic Semiconductors GmbHInventors: Hubert Spreitzer, Willi Kreuder, Heinrich Becker, Ute Neumann
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Patent number: 6465693Abstract: A method is provided for the transition metal-catalyzed arylation, or vinylation, of hydrazines, hydrazones, and the like. Additionally, the invention provides a conceptually novel strategy, the cornerstone of which is the transition metal-catalyzed arylation or vinylation method, for the synthesis of indoles, carbazoles, and the like. The methods and strategies of the invention may be utilized in standard, parallel, and combinatorial synthetic protocols.Type: GrantFiled: January 18, 2001Date of Patent: October 15, 2002Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Seble Wagaw, O. Geis
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Patent number: 6365776Abstract: The present invention provides an activator in arylamination using a palladium compound as a catalyst, which is superior to conventional phosphines in stability and performance. With the phosphine sulfide as an activator, an arylamination reaction achieves improved selectivity to produce a desired aromatic amine in an obviously increased yield as compared with a reaction using the corresponding phosphine compound. Moreover, the phosphine sulfide of the invention is impervious to oxidation and exists stably in air and therefore sufficiently withstands use on an industrial scale.Type: GrantFiled: September 6, 2001Date of Patent: April 2, 2002Assignee: Takasago International CorporationInventors: Mitsuhiko Fujiwara, Ken Suzuki, Tohru Kobayashi, Yoji Hori, Toshimitsu Hagiwara
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Patent number: 6331649Abstract: The present invention relates to a process for producing a trifluoromethylbenzylamine represented by the general formula (1). This process includes the step of reducing an oxime represented by the general formula (2), where R1 represents hydrogen atom, a halogen atom selected from the group consisting of fluorine, chlorine, bromine and iodine, or trifluoromethyl group, where R1 is defined as above, and R2 represents hydrogen atom, an alkyl group or an aralkyl group. With this process, the trifluoromethylbenzylamine can be produced with high selectivity.Type: GrantFiled: March 21, 2000Date of Patent: December 18, 2001Assignee: Central Glass Company, LimitedInventors: Satoru Narizuka, Yutaka Katsuhara
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Patent number: 6235938Abstract: The present invention is directed to a process for the preparation of N-aryl amine compounds. The process of the present invention involves reacting a compound having an amino group with an arylating compound in the presence of a base and a transition metal catalyst under reaction conditions effective to form an N-aryl amine compound, the transition metal catalyst comprising a Group 8 metal and at least one chelating ligand selected from the group consisting of bisphosphines having at least one stearically hindered alkyl substituent. The formed products are valuable intermediates in the pharmaceutical and polymer fields.Type: GrantFiled: June 10, 1999Date of Patent: May 22, 2001Assignee: Yale UniversityInventors: John F. Hartwig, Blake C. Hamann
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Patent number: 6235936Abstract: A method is provided for the transition metal-catalyzed arylation, or vinylation, of hydrazines, hydrazones, and the like. Additionally, the invention provides a conceptually novel strategy, the cornerstone of which is the transition metal-catalyzed arylation or vinylation method, for the synthesis of indoles, carbazoles, and the like. The methods and strategies of the invention may be utilized in standard, parallel, and combinatorial synthetic protocols.Type: GrantFiled: February 26, 1998Date of Patent: May 22, 2001Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Seble Wagaw, Oliver Fabian Geis
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Patent number: 6137011Abstract: Bistrifluoromethylbenzylamines are obtained in a simple manner in high purities and with good yields by catalytic hydrogenation of the corresponding bistrifluoromethylbenzonitriles if the process is carried out in the presence of Raney cobalt, at least one aliphatic ether and ammonia.Type: GrantFiled: February 25, 2000Date of Patent: October 24, 2000Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Ernst Kysela
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Patent number: 6137010Abstract: This invention relates to a process for preparing 4-nitrodiphenylamine and 4-nitrosodiphenylamine to be used for 4-aminodiphenylamine as an intermediate of antiozonant, wherein carbanilide is reacted with nitrobenzene in the presence of an appropriate base, while simultaneously adding aniline to the mixture so as to regenerate some amounts of carbanilide as a starting material.According to this invention, 4-nitrodiphenylamine and 4-nitrosodiphenylamine can be prepared in a higher selectivity and conversion rate via a continuous reaction by recycling carbanilide, a starting material, while adding a certain amount of aniline during the process. Further, the amount of waste water can be significantly reduced compared to the conventional method without any corrosive materials harmful to the environment.Type: GrantFiled: February 10, 2000Date of Patent: October 24, 2000Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Young J. Joo, Jin Eok Kim, Jeong Im Won, Kum Ui Hwang
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Patent number: 6127577Abstract: A method for manufacturing 3,5-difluoroaniline by fluorinating 1,3,5-trichlorobenzene and then aminating the intermediate fluorinated benzene with aqueous or anhydrous ammonia to achieve the product in yields of greater than 80%.Type: GrantFiled: February 8, 2000Date of Patent: October 3, 2000Assignee: BASF CorporationInventors: Lee I. Cherney, Francis J. Mettille
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Patent number: 5977412Abstract: The invention provides a novel process for producing a 3,5-difluoroaniline compound by reacting a 2-halo-4,6-difluoroaniline with a diazotizing agent in the presence of a reducing agent to form a diazonium salt. Build-up of potentially dangerous diazonium salt is avoided by reducing the diazonium salt with the reducing agent, to form a 1-halo-3,5-difluorobenzene, contemporaneously with the diazotization reaction. The 1-halo-3,5-difluorobenzene is then aminated.Type: GrantFiled: August 14, 1998Date of Patent: November 2, 1999Assignee: BASF CorporationInventors: Martin L. Bremmer, William J. Lipa
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Patent number: 5965775Abstract: The present invention relates to a process for the preparation of 3,5-difluoroaniline by reacting 3,5-difluorochlorobenzene with ammonia in the presence of a solvent in the presence of a copper compound and at least one metal selected from the group consisting of copper, iron, cobalt, nickel, chromium, molybdenum and zinc, at 100 to 250.degree. C.Type: GrantFiled: May 13, 1998Date of Patent: October 12, 1999Assignee: Clariant GmbHInventors: Ralf Pfirmann, Stefan Krause
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Patent number: 5929281Abstract: A heterocyclic aromatic halide or an aryl halide is reacted with an amine compound in the presence of a base to give a heterocyclic aromatic amine or an arylamine, respectively. In this reaction, a catalyst comprising a palladium compound and a tertiary phosphine is used for the preparation of a heterocyclic aromatic amine, and a catalyst comprising a palladium compound and a trialkylphosphine is used for the preparation of an arylamine.Type: GrantFiled: April 15, 1997Date of Patent: July 27, 1999Assignee: Tosoh CorporationInventors: Masakazu Nishiyama, Yasuyuki Koie
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Patent number: 5856576Abstract: There are provided aryne intermediates of formula I, useful in the manufacture of herbicidal compounds. ##STR1## Also provided is a method to prepare the formula I intermediates via the palladium catalyzed coupling of an o-halonitrobenzene or o-haloaniline with 3-butyne-1-ol.Type: GrantFiled: January 29, 1998Date of Patent: January 5, 1999Assignee: American Cyanamid CompanyInventors: Philip M. Harrington, Kenneth A. M. Kremer
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Patent number: 5831128Abstract: The present invention relates to a process for the preparation of aromatic amines of the formula (I)Ar--NR.sup.1 R.sup.2 (I)in which Ar is ##STR1## and R.sup.3 to R.sup.9 independently of one another are hydrogen, C.sub.1 -C.sub.8 -alkyl, alkoxy-(C.sub.1 -C.sub.8), acyloxy-(C.sub.1 -C.sub.8), OAr, Ar, fluorine, chlorine, bromine, iodine, OH, NO.sub.2, CN, CO.sub.2 H, CHO, SO.sub.3 H, SO.sub.2 R, SOR, NH.sub.2, NH-alkyl-(C.sub.1 -C.sub.12), N-alkyl.sub.2 -(C.sub.1 -C.sub.12), NHCO-alkyl-(C.sub.1 -C.sub.12), CO-alkyl-(C.sub.1 -C.sub.12), NHCHO, COAr, CO.sub.2 Ar, CF.sub.3, CONH.sub.2, CHCHCO.sub.2 R, POAr.sub.2, PO-alkyl.sub.2 -(C.sub.1 -C.sub.12), 5-ring heteroaryl, 6-ring heteroaryl, Si-alkyl.sub.3 -(C.sub.1 -C.sub.12), where R=alkyl(C.sub.1 -C.sub.8), aryl(C.sub.5 -C.sub.10) and R.sup.1 and R.sup.2 independently of one another are hydrogen, C.sub.1 -C.sub.Type: GrantFiled: December 3, 1997Date of Patent: November 3, 1998Assignee: Hoechst AktiengesellschaftInventors: Matthias Beller, Thomas Riermeier, Claus Peter Reisinger, Wolfgang Anton Herrmann, Holger Geissler
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Patent number: 5817850Abstract: The synthesis of new sterically hindered ferrocene bis(phosphonites) of formula I ##STR1## the synthesis of the corresponding transition-metal complexes and the use of these complexes in transition-metal-catalyzed reactions are described.Type: GrantFiled: October 30, 1997Date of Patent: October 6, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Stephen D. Pastor, Sai P. Shum
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Patent number: 5744638Abstract: The present invention relates to a process for the preparation of compounds of the general formula I ##STR1## in which X and Y, independently of each other, represent hydrogen, fluorine, chlorine or bromine, but cannot simultaneously represent hydrogen, characterised in that compounds of the general formula II ##STR2## in which X and Y are defined as above, are reacted with aqueous ammonia under copper catalysis, and to intermediates for the preparation of compounds of the general formula I.Type: GrantFiled: January 13, 1995Date of Patent: April 28, 1998Assignee: Riedel-de Haen AktiengesellschaftInventors: Horst Schmand, Bernd Kellermeier, Gunter Bartels, Hans-Jurgen Schmidt
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Patent number: 5684203Abstract: Nitroaromatics can be aminated using urea in the presence of bases and oxygen.Type: GrantFiled: July 26, 1995Date of Patent: November 4, 1997Assignee: Bayer AktiengesellschaftInventor: Manfred Jautelat
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Patent number: 5576460Abstract: A method of preparing an arylamine compound includes reacting a metal amide comprising a metal selected from the group consisting of tin, boron, zinc, magnesium, indium and silicon, with an aromatic compound comprising an activated substituent in the presence of a transition metal catalyst to form an arylamine. The method is useful in preparing mixtures of arylamines for use in screening for pharmaceutical and biological activity and in preparing poly(anilines).Type: GrantFiled: July 27, 1994Date of Patent: November 19, 1996Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Anil Guram
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Patent number: 5510533Abstract: A process for production of a 3,5-difluoroaniline compound with ease is disclosed, which comprise reacting an aminating agent with a 1,3,5-trifluorobenzene compound.Type: GrantFiled: June 5, 1991Date of Patent: April 23, 1996Assignee: SDS Biotech K.K.Inventors: Hiroshi Kobayashi, Masaaki Shimizu, Haruaki Ito
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Patent number: 5484953Abstract: Novel o-phenylenediamines of the formula containing fluoroalkyl(ene) groups ##STR1## in which the symbols used have the meaning given in the description, processes for their preparation and their use as intermediates.Type: GrantFiled: June 3, 1994Date of Patent: January 16, 1996Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Bernd Baasner, Folker Lieb
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Patent number: 5466871Abstract: A process for preparing a nitroaniline derivative comprising a step of reacting an aromatic nitro compound with an O-alkylhydroxylamine or a salt thereof in the presence of a base and optionally a metallic catalyst, which process is industrially advantageous since it provides the nitroaniline derivative from the aromatic nitro compound in a high yield in one step, and the aminating agent used can be obtained from hydroxylamine at a relatively low cost.Type: GrantFiled: July 11, 1994Date of Patent: November 14, 1995Assignee: Sumitomo Chemical Company, LimitedInventor: Shinzo Seko
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Patent number: 5274135Abstract: A process for preparing a 3- or 4-aminobenzocyclobutene comprises aminating a 3- or 4-halo- or sulfonyloxybenzocyclobutene reactant with an aminating agent by heating at a temperature from about 80.degree. C. to a temperature at which dimerization or oligomerization of a benzocyclobutene reactant or product is a significant side reaction, in the presence of a metal-containing catalyst, for a time sufficient to aminate the halo- or sulfonyloxybenzocyclobutene reactant. In another aspect, this invention relates to a process for making a 3- or 4-phthalimido- or maleimidobenzocyclobutene, comprising reacting a 3- or 4-halobenzocyclobutene reactant with a phthalimide or maleimide compound in the presence of a metal-containing catalyst. The resulting phthalimido- or maleimidobenzocyclobutene can be hydrolyzed to a 3- or 4-aminobenzocyclobutene.Type: GrantFiled: September 20, 1991Date of Patent: December 28, 1993Assignee: The Dow Chemical CompanyInventors: Kenneth J. Bruza, Arnold E. Young, Kurt A. Bell
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Patent number: 5210303Abstract: A process for producing a benzylamine which comprises reacting a benzyl halide with an aqueous ammonia solution in the presence of an aromatic aldehyde represented by the formula: ##STR1## wherein R represents a hydrogen atom, a halogen atom or a lower alkyl group, and n is 1 or 2, separating an oily substance from the reaction mixture, and treating the oily substance with a mineral acid.Type: GrantFiled: April 18, 1991Date of Patent: May 11, 1993Assignee: Ihara Chemical Industry Co., Ltd.Inventor: Tatsuo Sugiyama
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Patent number: 5144076Abstract: 3,5-Diaminobenzotrifluoride can be produced, in a single step, by reacting 4-chloro-3,5-dinitro benzotrifluoride in a suitable solvent, with hydrogen gas, in the presence of a catalyst comprising palladium on a suitable carrier, and in the presence of a suitable base.Type: GrantFiled: October 1, 1991Date of Patent: September 1, 1992Assignee: Occidental Chemical CorporationInventors: Ramesh Krishnamurti, Lawrence B. Fertel, Henry C. Lin, Mahendra K. Dosi
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Patent number: 5091580Abstract: 2,6-Difluoroaniline is prepared from 1,2,3-trichlorobenzene by partial fluorine exchange to a mixture of 2,6-difluorochlorobenzene and 2,3-difluorochlorobenzene, amination of the chloro substituents, and separation of the desired product from the isomeric 2,3-difluoroaniline. By incorporating a selective reduction into the process immediately after the partial fluorine exchange, the undesirable 2,3-difluorochlorobenzene is converted into valuable ortho-difluorobenzene and the 2,3-difluoroaniline isomer is avoided.Type: GrantFiled: March 27, 1991Date of Patent: February 25, 1992Assignee: DowElancoInventors: R. Garth Pews, James A. Gall
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Patent number: 4521622Abstract: A process for producing an aromatic amine from an aromatic halide and ammonia, characterized by comprising the following steps (1), (2) and (3):step (1): reacting the aromatic halide with ammonia in the presence of water by using a catalyst comprising a copper compound as the main constituent,step (2): extracting the aromatic amine from the reaction mixture obtained in step (1) without depositing or separating the copper component contained in the reaction mixture, andstep (3): adding an alkali metal hydroxide and/or an alkaline earth metal hydroxide to the raffinate aqueous solution obtained by the extraction procedure in step (2) to deposit copper compounds and separating the same.This process is good in reaction efficiency and permits easy recovery of the catalyst.Type: GrantFiled: February 3, 1984Date of Patent: June 4, 1985Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Naoki Andoh, Shuetsu Fujiwara
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Patent number: 4508922Abstract: Process for the manufacture of an optionally halogenated aniline of the formula: ##STR1## in which Y=halogen, R=H, alkyl (C.sub.1 -C.sub.4) or alkoxy (C.sub.1 -C.sub.4) and n=0 to 5.Halogenobenzenes of the formula: ##STR2## in which Y, R and n are as above and X=halogen, are subjected to ammonolysis with aqueous ammonia solution, in the presence of copper and 8-hydroxyquinoline.The process can be used, in particular, for the preparation of 3,5-dichloroaniline.Type: GrantFiled: June 28, 1983Date of Patent: April 2, 1985Assignee: Rhone-Poulenc AgrochimieInventor: Serge Ratton
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Patent number: 4433168Abstract: Crude 3,4,3',4'-tetraaminodiphenyl (TAD) prepared by ammonolysis of 3,3'-dichlorobenzidine in the presence of mainly Cu catalysts is purified by a process in which(a) after its isolation from the preparation process crude TAD is treated with an aqueous NH.sub.3 solution and, if desired, TAD thus treated is then(b) dissolved and reprecipitated in water in the presence of adsorbents and also of a water-soluble reducing agent.Compared with relevant processes of the state of the art, the process produces a higher yield of pure TAD and it is also simpler to carry out.Type: GrantFiled: March 22, 1982Date of Patent: February 21, 1984Assignee: Hoechst AGInventors: Hans Schubert, Konrad Baessler
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Patent number: 4380670Abstract: An aminobenzene is produced by reacting a chlorobenzene with ammonia in the presence of a copper type catalyst, namely by reacting ammonia with 3,5-diaminochlorobenzene to produce 1,3,5-triaminobenzene at a temperature of 150.degree. to 250.degree. C. at a molar ratio of ammonia of 2 to 10 to 3,5-diaminochlorobenzene in the presence of a copper compound catalyst.Type: GrantFiled: April 3, 1981Date of Patent: April 19, 1983Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Itaru Shigehara, Mikio Miyaji