Processes Of Forming The Bicyclo Ring System By Cyclization (e.g., Forming Indole From O-ethyl Aniline, Etc.) Patents (Class 548/508)
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Patent number: 4757152Abstract: A process for producing an indole by catalytic reaction of a 2-(o-aminoaryl)ethanol, said reaction being carried out by heating in a liquid phase in the presence of an alkali metal using a catalyst containing a metal selected from the group consisting of a platinum-group metal, nickel and copper.The process is industrially advantageous in that indoles are produced in high yield.Type: GrantFiled: November 12, 1985Date of Patent: July 12, 1988Assignee: Research Association for Utilization of Light OilInventors: Makoto Imanari, Hiroshi Iwane, Katsuhumi Kuzira, Takatoshi Seto
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Patent number: 4732654Abstract: In an industrial process for preparing indole by reacting aniline and ethylene glycol, high boiling-point impurities and non-volatile substances are removed in advance from the reaction mixture either before the recovery of aniline from the reaction mixture or before the subsequent rectification of the resultant indole. Indole of a high purity can thus be obtained.Type: GrantFiled: July 15, 1987Date of Patent: March 22, 1988Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Atsuyoshi Yamauchi, Seiya Iguchi, Yuzo Ono, Hiroshi Kimura, Satoshi Morita
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Patent number: 4727161Abstract: A process for producing an indole which comprises reacting an aniline and a diol in the presence of a catalyst to produce a reaction mixture containing the indole, unreacted aniline and by-products, condensing the reaction mixture to obtain a liquid reaction product, recovering the unreacted aniline from the liquid reaction product, reducing the contents of specified by-products in the recovered aniline below specified levels and reutilizing the resulting recovered aniline. To reduce the contents of the specified by-products in the recovered aniline below specified levels, it is preferred to subject the liquid reaction product or an aniline fraction separated therefrom to a heat-treatment and then to distillation. In the above manner, the recovered aniline can be reutilized in the reaction without causing the activity of the catalyst to deteriorate.Type: GrantFiled: November 15, 1985Date of Patent: February 23, 1988Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Atsuyoshi Yamauchi, Seiya Iguchi, Yuzo Ono, Hiroshii Kimura, Satoshi Morita
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Patent number: 4703126Abstract: Process for the production of 7-ethyl indole by dehydrocyclization of 2,6-diethylaniline and then partial hydrogenation of the accumulated raw product.Type: GrantFiled: August 13, 1986Date of Patent: October 27, 1987Assignee: Lonza Ltd.Inventor: Peter Hardt
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Patent number: 4659841Abstract: A process for preparing indoles in high yield by reacting anilines and 1,2-glycols in a liquid phase in the presence of a cadmium bromide or iodide/potassium bromide or iodide catalyst. The used catalyst can be easily recovered and when reused, exhibits excellent performance.Type: GrantFiled: July 5, 1985Date of Patent: April 21, 1987Assignee: Research Association for Utilization of Light OilInventors: Makoto Imanari, Hiroshi Iwane, Katsufumi Kuzira, Takatoshi Seto
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Patent number: 4598156Abstract: Indoles of the formula I which are unsubstituted in the 2- and 3-positions: ##STR1## wherein Z is hydrogen or a group --COR, and X and Y have the meanings defined in claim 1, can be produced by a novel, simple and economical process which comprises reacting a compound of the formula II ##STR2## at a temperature of between 0.degree. and 120.degree. C., in the presence of a mercury or palladium catalyst, with benzoic acid vinyl ester, or with the vinyl ester of an aliphatic C.sub.1 -C.sub.4 -monocarboxylic acid; and optionally saponifying compounds of the formula I in which Z is --COR. The compounds of the formula I can be used for example for producing indigo dyes, or they can be used as pharmaceutical or agricultural active substances.Type: GrantFiled: February 7, 1983Date of Patent: July 1, 1986Assignee: Ciba Geigy CorporationInventor: Pierre Martin
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Patent number: 4595765Abstract: 5,6-Dihydroxyindole is prepared by the catalytic reductive cyclization of 4,5-dihydroxy-2,.beta.-dinitrostyrene in a single step using hydrogen with a palladium, platinum or rhodium catalyst in a polar hydroxylic reaction system. No reaction byproducts or only a single reaction byproduct are produced. The 4,5-dihydroxy-2,.beta.-dinitrostyrene intermediate can be prepared by the chemoselective debenzylation of 4,5-dibenzyloxy-2,.beta.-dinitrostyrene using trifluoroacetic acid. 5,6-Dihydroxyindole is a useful component in hair dye formulations and as an intermediate in the synthesis of melanin.Type: GrantFiled: October 18, 1985Date of Patent: June 17, 1986Assignee: Clairol IncorporatedInventor: Bryan P. Murphy
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Patent number: 4585877Abstract: A process for preparing 1,8-diethyl-1,3,4,9-tetrahydro[3,4-b]-indole-1-acetic acid (etodolac) is disclosed. Etodolac is a useful antiinflammatory and analgesic agent.Type: GrantFiled: May 6, 1985Date of Patent: April 29, 1986Assignee: American Home Products CorporationInventors: Christopher A. Demerson, Leslie G. Humber
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Patent number: 4506079Abstract: Convenient intermediates for preparing 3-substituted-2-hydroxypropyl aryl ether .beta.-blockers, a reaction to the intermediates of the following formula and a conversion to obtain the said .beta.-blockers are disclosed. ##STR1## (wherein X is hydrogen or halogen;Y is halogen, hydroxy, lower acyloxy, amino, lower alkylamino, lower aralkylamino, lower acylamino, di-lower alkylamino, lower alkyleneamino, N-lower alkyl-N-lower aralkylamino, di-lower acylamino, N-lower alkyl-N-lower acylamino or N-tri-lower alkylsilylamino;one of P and R combined together with Q represents lower alkylene or alkenylene optionally interrupted by O, N or S and optionally substituted by lower alkyl, lower aralkyl, lower carboxylic acyl, carboxy, protected carboxy; hydroxy, lower alkoxy, lower acyloxy, oxo; amino, lower alkylamino, lower acylamino, nitro, nitroso, lower alkylthio, lower sulfonic acyl or halogen;and the remaining R or P is hydrogen or halogen;and dotted line represents the presence of one or two double bonds).Type: GrantFiled: March 5, 1980Date of Patent: March 19, 1985Assignee: Shionogi & Co., Ltd.Inventor: Makiko Sakai
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Patent number: 4506077Abstract: Disclosed herein is a process for obtaining indoline-2-carboxylic acid ester tin complexes directly from o-nitropyruvic acids using metallic tin and dry hydrogen chloride gas in a lower alkanol solvent, at atmospheric pressures.Type: GrantFiled: February 3, 1983Date of Patent: March 19, 1985Assignee: American Home Products CorporationInventors: Ronald J. McCaully, Dong H. Kim
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Patent number: 4476310Abstract: A process for the preparation of indoles which comprises reacting aniline or a derivative thereof with a 1,2-glycol in the presence of a catalyst comprising silver supported on a carrier having a specific surface area of not less than 10 m.sup.2 /g.Type: GrantFiled: June 9, 1982Date of Patent: October 9, 1984Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Tadatoshi Honda, Fujio Matsuda, Tadamitsu Kiyoura, Kazuhiro Terada
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Patent number: 4474969Abstract: Preparation process of indole from aniline and ethylene glycol. Upon preparing indole by reacting aniline and ethylene glycol in a gas phase and in the presence of a catalyst, ethylene glycol is charged in portions to a multiplicity of catalyst stages formed by dividing a catalyst bed and connected in series. This divided supply of ethylene glycol permits the suppresing of the decomposition of ethylene glycol, even if the molar ratio of feed aniline to total feed ethylene glycol is small. The above process permits making the yield of indole large and reducing the amount of unreacted aniline to be separated and recovered from the reaction effluent.Type: GrantFiled: April 22, 1983Date of Patent: October 2, 1984Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Tadatoshi Honda, Kazuhiro Terada
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Patent number: 4473699Abstract: Indole, and/or methyl-substituted indoles are described as prepared from the corresponding 2-(cyanomethyl)cyclohexanone starting material through a catalytic reaction in the presence of hydrogen, using a metal, or metal compound, of Group VIII or Group Ib of the Periodic Table. The reaction is carried out at an elevated temperature at high conversion to yield the corresponding indole and (in some cases) tetra- or hexahydroindoles.Type: GrantFiled: May 11, 1982Date of Patent: September 25, 1984Assignee: Stamicarbon B.V.Inventors: Roland E. van der Stoel, Petrus H. J. Janssen, Cornelis G. M. van de Moesdijk
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Patent number: 4473698Abstract: A process for the preparation of indole and derivatives thereof wherein an aniline is reacted with a 1,2-glycol in the vapor phase, the liquid phase or a mixed vapor-liquid phase. A salt of a metal of group IIa of the periodic table, a salt of iron, a salt of cobalt and/or a salt of nickel are used as the catalyst for this reaction. The present invention makes it possible to prepare indole and derivatives thereof in a single step by using inexpensive compounds as the starting materials.Type: GrantFiled: April 22, 1981Date of Patent: September 25, 1984Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Fujio Matsuda, Takazo Kato, Tadatoshi Honda
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Patent number: 4456760Abstract: A process for the preparation of indole and derivatives thereof wherein an aniline is reacted with a 1,2-glycol in the liquid phase in the presence of a catalyst containing metallic copper and/or copper oxide. The present ivention makes it possible to prepare indole and derivatives thereof in a single step by using inexpensive starting materials.Type: GrantFiled: May 5, 1982Date of Patent: June 26, 1984Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Fujio Matsuda, Takazo Kato, Tadamitsu Kiyoura
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Patent number: 4443615Abstract: An indole of the formula ##STR1## can be prepared by subjecting an aniline of the formula: ##STR2## and a glycol or an oxide of the formula: ##STR3## to vapor phase reaction at 250.degree. to 400.degree. C. in the presence of a solid acid catalyst having dehydrating and dehydrogenating activities.(In the above-mentioned formulae, R.sup.1 stands for hydrogen, alkyl, aryl or aralkyl, R.sup.2 stands for alkyl or alkoxy, R.sup.3 and R.sup.4 are the same or different and stands for hydrogen or alkyl, R.sup.5 and R.sup.6 are the same or different and stand for hydrogen or alkyl, and n is an integer of 0 to 4.Type: GrantFiled: November 10, 1981Date of Patent: April 17, 1984Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Manabu Matsuoka, Michihiro Tsuchiya, Yoshikazu Tokuda
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Patent number: 4436916Abstract: A process for the preparation of indole and derivatives thereof wherein an aniline is reacted with a 1,2-glycol in the vapor phase, the liquid phase or a mixed vapor-liquid phase. A sulfide or selenide or cadmium and/or zinc are used as the catalyst for this reaction. The present invention makes it possible to prepare indole and derivatives thereof in a single step by using inexpensive compounds as the starting materials.Type: GrantFiled: May 18, 1981Date of Patent: March 13, 1984Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Fujio Matsuda, Takazo Kato, Tadatoshi Honda, Kazuhiro Terada, Yasuo Kogure
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Patent number: 4436917Abstract: A process for the preparation of indole and derivatives thereof which comprises reacting an aniline with a 1,2-glycol in the vapor phase, the liquid phase or a mixed vapor-liquid phase. Various solid acids, metals and activated carbon can be used as catalysts for this reaction. The present invention makes it possible to prepare indole and derivatives thereof in a single step by using inexpensive compounds as the starting materials.Type: GrantFiled: April 15, 1981Date of Patent: March 13, 1984Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Fujio Matsuda, Takazo Kato
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Patent number: 4431821Abstract: Novel 1-fluoromethyl-substituted alkyl amines are disclosed. The novel compounds have biological activity including decarboxylase inhibition.Type: GrantFiled: July 20, 1981Date of Patent: February 14, 1984Assignee: Merck & Co., Inc.Inventors: Arthur A. Patchett, Janos Kollonitsch
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Patent number: 4404063Abstract: A method for the separation of indole by distilling an indole-containing reaction fluid obtained by the reaction of aniline with ethylene glycol or by the reaction of N-(.beta.-hydroxyethyl)aniline, which comprises bringing the reaction fluid into contact with a basic substance prior to and/or during the distillation. This method can prevent the deterioration of indole during the distillation procedure.Type: GrantFiled: September 24, 1982Date of Patent: September 13, 1983Assignee: Mitsui Toatsu Chemicals, Inc.Inventor: Tadatoshi Honda
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Patent number: 4394514Abstract: A new chemical sequence for preparing indoles is disclosed whose key reactions are reaction of a o-nitrotoluene with tris(dimethylamino)methane to give a .beta.-dimethylamino-o-nitrostyrene which is converted into a semicarbazone and cyclized.Type: GrantFiled: June 29, 1981Date of Patent: July 19, 1983Assignee: SmithKline Beckman CorporationInventor: Lawrence I. Kruse
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Patent number: 4376205Abstract: A process for the preparation of indole and derivatives thereof wherein an aniline is reacted with an ethanolamine in the vapor phase, the liquid phase or a mixed vapor-liquid phase. Various solid acids, metals and activated carbon can be used as catalysts for this reaction. The present invention makes it possible to prepare indole and derivatives thereof in a single step by using inexpensive compounds as the starting materials.Type: GrantFiled: April 15, 1981Date of Patent: March 8, 1983Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Fujio Matsuda, Takazo Kato