Replacing Oxygen Or Nitrogen, Single Bonded To Carbon, By Cyano Patents (Class 558/350)
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Publication number: 20130053538Abstract: A process for reacting ethylenediamine (EDA) with formaldehyde to give ethylenediamine-formaldehyde adduct (EDFA) and/or ethylenediamine-monoformaldehyde adduct (EDMFA), which comprises performing the reaction of FA with EDA at a temperature in the range from 20 to 70° C.Type: ApplicationFiled: August 30, 2012Publication date: February 28, 2013Applicant: BASF SEInventors: Hermann Luyken, Sebastian Ahrens, Gordon Brasche, Jens Baldamus, Robert Baumann, Randolf Hugo, Stephanie Jaegli, Johann-Peter Melder, Jörg Pastre, Boris Buschhaus
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Patent number: 8252951Abstract: Process for the industrial synthesis of the compound of formula (I) Application of such process in the synthesis of agomelatine.Type: GrantFiled: August 1, 2008Date of Patent: August 28, 2012Assignee: Les Laboratoires ServierInventors: Thierry Dubuffet, Jean-Pierre Lecouve, Jean-Paul Hermet
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Publication number: 20120059179Abstract: A new method of ortho-fluorination where an aryl C—H bond is directly replaced by an aryl C-F bond in a palladium-catalyzed reaction is provided. The method includes the ortho-fluorination of a triflamide protected benzylamine, a palladium catalyst, such as Pd(OTf)2, a fluorinating reagent such as N-fluoro-2,4,6-trimethylpyridinium triflate, and a ligand to promote the reaction such as N-methylpyrrolidinone (NMP).Type: ApplicationFiled: April 2, 2010Publication date: March 8, 2012Applicant: The Scripps Research InsitiuteInventor: Jin-Quan Yu
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Publication number: 20100137628Abstract: Process for the industrial synthesis of the compound of formula (I) Application of such process in the synthesis of agomelatine.Type: ApplicationFiled: August 1, 2008Publication date: June 3, 2010Applicant: LES LABORATOIRES SERVIERInventors: Thierry Dubuffet, Jean-Pierre Lecouve, Jean-Paul Hermet
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Publication number: 20040254391Abstract: A process is provided for the preparation of a compound of Formula (1) 1Type: ApplicationFiled: July 19, 2004Publication date: December 16, 2004Inventors: Andrew John Blacker, Ian Nicholas Houson, Jonathan William Wiffen
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Patent number: 6566546Abstract: A process for preparing 4-substituted 2-alkylbiphenyls and 2-alkoxybiphenyls of the formula (I),Type: GrantFiled: February 11, 2002Date of Patent: May 20, 2003Assignee: Clariant GmbHInventors: Andreas Meudt, Stefan Scherer, Frank Vollmüller, Heinz Georg Kautz
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Publication number: 20020072626Abstract: Novel process steps and novel processes for producing unsubstituted and substituted meta- and para- cyano benzoic acid compounds, as well as salts and derivatives thereof, and intermediates therefor which are useful as intermediates for producing platelet aggregation inhibitors. Further disclosed are processes for producing bicyclic and heterocyclic cyano substituted compounds also having a carboxyl group attached to the same ring structure.Type: ApplicationFiled: December 13, 2000Publication date: June 13, 2002Inventors: James Kantor, John Jason Gentry Mullins, Robert Scarborough
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Patent number: 6399807Abstract: The invention relates to a process for preparing 2,4,5-trifluoro-benzonitrile of the formula (I) in which 2,4,5-trifluoro-aniline of the formula (II) is, in a first step A), reacted with a nitrosating agent in the presence of a diluent and in which, in a second step B), the reaction product obtained in step A) is reacted with an alkali metal cyanide in the presence of a transition metal compound, an acid acceptor and a diluent.Type: GrantFiled: December 21, 1999Date of Patent: June 4, 2002Assignee: Bayer AktiegesellschaftInventors: Achim Hupperts, Reinhard Lantzsch
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Patent number: 5637751Abstract: 2-Butene-1,4-diol and/or 3-butene-1,2-diol are (is) reacted with hydrogen cyanide in the presence of a molten catalyst comprising a cuprous halide and a non-aromatic organic amine hydrohalide.Type: GrantFiled: April 1, 1993Date of Patent: June 10, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Katsuharu Imi, Shigeo Wake
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Patent number: 5463103Abstract: The object of the present invention is to provide a process for producing 1,4-dicyano-2-butene in a high yield and in an industrially advantageous way.The present invention relates to a process for producing 1,4-dicyano-2-butene which comprises reacting a butene derivative represented by the formula [1]R.sub.1 --CH.sub.2 --CH.dbd.CH--CH.sub.2 --R.sub.2 [1]or the formula [2]R.sub.3 --CH.sub.2 --CHR.sub.4 --CH.dbd.CH.sub.2 [2]wherein each of R.sub.1 and R.sub.3 represents a hydroxy group, lower acyloxy group, lower alkoxy group or cyano group; and each of R.sub.2 and R.sub.4 represents a hydroxy group, lower acyloxy group or lower alkoxy group, with hydrogen cyanide in the presence of a catalyst comprising a product prepared from a cuprous halide, a non-aromatic amine hydrohalide and at least one member selected from the group consisting of Lewis acids and basic compounds.Type: GrantFiled: February 24, 1994Date of Patent: October 31, 1995Assignee: Sumitomo Chemical Company, LimitedInventors: Shinji Nishii, Shigeo Wake, Takeshi Ogawa
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Patent number: 5416235Abstract: A process for the preparation of aromatic compounds of the general formula I,Ar--X Iin which Ar represents an optionally substituted aryl group and X represents a group OH, Cl, Br or CN, by reaction of an aryl diazoniumsalt of the formula II,Ar--N.dbd.N.sup.+ Y.sup.- IIin which Ar is as defined above and Y represents a suitable counterion, with water, hydrogen chloride or a salt thereof, hydrogen bromide or a salt thereof, or a cyanide in the presence of a copper(I)salt, characterized in that the copper(I)salt is a copper(I)salt derived from an hydroxy carboxylic acid.Type: GrantFiled: November 1, 1993Date of Patent: May 16, 1995Assignee: Octel Chemicals LimitedInventors: Bruce C. Gilbert, Peter Hanson, Jason R. Jones, Allan W. Timms
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Patent number: 5292918Abstract: A process for preparing an (S,S) or (R,R) diastereoisomer of the formula: ##STR1## or salts, esters or amides thereof, wherein R.sup.3 and R.sup.4 independently represent hydrogen, alkyl, aryl or aryl substituted with halogen, alkyl, nitro or alkoxy, and n and m independently represent integers from one to six, comprising combining a cyanide compound of the formula:M.sup.1 C.tbd.N (III)wherein M.sup.1 is hydrogen, trimethylsilyl or a metal, with an optional proton source, a solvent and a Lewis acid of the formula:M.sup.2 X.sub.4, AlCl.sub.3 or BF.sub.3 (IV)wherein M.sup.2 is Sn or Ti and X represents chloro, bromo, fluoro or iodo, with an .alpha.-amino acid compound or salts or esters thereof, followed by addition of an acyl or acetal compound to give the diastereoisomer of formula (X).Type: GrantFiled: October 6, 1992Date of Patent: March 8, 1994Assignee: Schering CorporationInventors: Jacques Gosteli, Ingrid Mergelsberg, Markus Tanner
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Patent number: 4855476Abstract: The present invention relates to novel 5-fluoro- and 8-fluoro-trimetoquinol compounds of the general formula I wherein X.sub.1 =F, X.sub.2 =H or X.sub.1 =H, X.sub.2 =F ##STR1## The present invention also relates to a process for making the 5-fluoro- and 8-fluoro-trimetoquinol compounds by condensation of an appropriately substituted phenethylamine to afford an appropriately substituted phenlethylacetamide compound. The amides are cyclized to give appropriately substituted intermediate dihydroisoquinolines. Without isolation, the dihydroisoquinolines are reduced to give appropriately substituted tetrahydroisoquinolines. The hydrochloride salts of tetrahydroisoquinolines are prepared and subjected to hydrogenolysis, to give the fluorine substituted trimetoquinol compounds of the present invention.Type: GrantFiled: March 14, 1988Date of Patent: August 8, 1989Assignee: Ohio State University Research FoundationInventors: Duane D. Miller, Dennis R. Feller, Michael T. Clark, Adeboye Adejare, Karl J. Romstedt, Gamal Shams
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Patent number: 4792606Abstract: A process for the preparation of a dimeric aromatic acyl cyanide of the formula ##STR1## in which Ar is optionally substituted phenyl, naphthyl or hetaryl,comprising reaction an acyl halide of the formulaAr--CO--Halin whichHal is fluorine, chlorine or bromine, with an alkali metal cyanide in a two-phase system comprising water and a water-immiscible or only sparingly water-miscible aliphatic ketone, and in the presence of a phase-transfer catalyst. The products are known intermediates for pesticides.Type: GrantFiled: July 16, 1987Date of Patent: December 20, 1988Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Hermann-Dieter Krall
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Patent number: 4577046Abstract: Deamination of aromatic primary amines by diazotization and hydrogen replacement of the diazo group is accelerated in the presence of hydrogen peroxide. Yields of at least about 85% are typical, with reaction times of usually about one hour or less.Type: GrantFiled: June 11, 1984Date of Patent: March 18, 1986Assignee: University of New MexicoInventors: Mark D. Hylarides, Fred A. Mettler, Jr.