Patents Represented by Attorney Patricia J. Hogan

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  • Thiation process
    Patent number: 4663452
    Abstract: An organic carbonyl compound is thiated to the corresponding thiono compound by reacting it with phosphorus pentasulfide in the presence of an alkali metal bicarbonate and a hydrocarbon diluent. In preferred embodiments of the invention, the carbonyl compound is an amide, especially an aromatic amide, and the diluent is an inert hydrocarbon having a boiling point in the range of about 50.degree.-150.degree. C.
    Type: Grant
    Filed: August 29, 1985
    Date of Patent: May 5, 1987
    Assignee: Ethyl Corporation
    Inventor: Kenneth C. Lilje
  • Brominative aromatization of 4-cyclohexenylpyridines
    Patent number: 4649202
    Abstract: A 4-cyclohexenylpyridine is brominatively aromatized to the corresponding 4-phenylpyridine by brominating the cyclohexenylpyridine, such as a 4-(halocyclohexenyl)pyridine, especially a 4-(4-halocyclohex-3-enyl)pyridine hydrochloride, and heating the brominated product in the presence or absence of any added base or hydrogen acceptor to form, e.g., a 4-(halophenyl)pyridine. The invention is of particular utility in the manufacture of intermediates of antibacterial 1-alkyl-1,4-dihydro-4-oxo-7-(4-pyridyl)-3-quinolinecarboxylic acids.
    Type: Grant
    Filed: March 22, 1985
    Date of Patent: March 10, 1987
    Assignee: Ethyl Corporation
    Inventors: Paul F. Ranken, Venkataraman Ramachandran
  • Process for preparing arylisothiocyanates
    Patent number: 4636574
    Abstract: Arylisothiocyanates are prepared by reacting a primary arylamine with carbon disulfide in the presence of a tertiary amine.
    Type: Grant
    Filed: November 4, 1985
    Date of Patent: January 13, 1987
    Assignee: Ethyl Corporation
    Inventor: Kju H. Shin
  • Process for hydrolyzing nitriles
    Patent number: 4629808
    Abstract: A 6-alkoxy-5-trifluoromethyl-1-cyanonaphthalene is hydrolyzed to the corresponding acid in high yield by reacting it with an aqueous alcoholic base under moderate pressure at a temperature of about 115.degree.-130.degree. C. A preferred nitrile is 6-methoxy-5-trifluoromethyl-1-cyanonaphthalene, preferred bases are sodium and potassium hydroxides, utilizable alcohols are alkanols containing 1-3 carbons, and preferred pressures are in the range of about 90-110 psi.
    Type: Grant
    Filed: June 20, 1985
    Date of Patent: December 16, 1986
    Assignee: Ethyl Corporation
    Inventor: K. Pushpananda A. Senaratne
  • Preparation of 4-(.alpha.,.alpha.-dihydrocarbyl-.alpha.-cyano-methyl)phenols
    Patent number: 4611075
    Abstract: Novel 4-(.alpha.,.alpha.-dihydrocarbyl-.alpha.-cyano-methyl)-2,6-mono or dihydrocarbyl substituted phenols are prepared by reacting a 2,6-mono or dihydrocarbyl substituted phenol with a ketone and an alkali metal cyanide or an alkaline earth metal cyanide in an inert reaction solvent.
    Type: Grant
    Filed: April 11, 1985
    Date of Patent: September 9, 1986
    Assignee: Ethyl Corporation
    Inventor: Charles R. Everly
  • Arylation of olefins
    Patent number: 4604243
    Abstract: An olefin, especially an activated olefin, is arylated by reaction with an arylamine, such as an aniline, in an inert polar organic solvent and in the presence of an alkyl nitrite, a hydrogen halide, and a catalytic amount of a copper catalyst having the copper in an oxidation state below +2.
    Type: Grant
    Filed: July 25, 1985
    Date of Patent: August 5, 1986
    Assignee: Ethyl Corporation
    Inventor: Robert I. Davidson
  • Certain 4-(3,4-dibromocyclohexyl)pyridines
    Patent number: 4604467
    Abstract: A 4-cyclohexenylpyridine is brominatively aromatized to the corresponding 4-phenylpyridine by brominating the cyclohexenylpyridine, such as a 4-(halocyclohexenyl)pyridine, especially a 4-(4-halocyclohex-3-enyl)pyridine hydrohalide, and heating the brominated product in an inert solvent and in the presence of a base to form, e.g., a 4-(halophenyl)pyridine. The invention is of particular utility in the manufacture of intermediates of antibacterial 1-alkyl- 1,4-dihydro-4-oxo-7-(4-pyridyl)-3-quinolinecarboxylic acids.
    Type: Grant
    Filed: March 25, 1985
    Date of Patent: August 5, 1986
    Assignee: Ethyl Corporation
    Inventors: Venkataraman Ramachandran, Paul F. Ranken
  • Process for preparing substituted tetralones
    Patent number: 4603221
    Abstract: 6-Alkoxytetralones are prepared by gradually adding a persulfate to a heated mixture of a 6-alkoxytetralin, a salt of a divalent metal, and a tertiary amine and maintaining the 6-alkoxytetralin in intimate admixture with the persulfate until it has been oxidized to the corresponding 6-alkoxytetralone. The reaction is preferably conducted in solution or dispersion. Preferred reaction ingredients are 6-methoxytetralin, cupric sulfate, an alkylpyridine, and sodium persulfate.
    Type: Grant
    Filed: June 10, 1985
    Date of Patent: July 29, 1986
    Assignee: Ethyl Corporation
    Inventor: Kju H. Shin
  • (Hydrocarbylthio) phenols and their preparation
    Patent number: 4602113
    Abstract: (Hydrocarbylthio)phenols containing hydrocarbylthio groups in either or both of the meta positions, relative to the hydroxy group, on a phenolic ring are prepared by reacting phenolic compounds with an excess of hydrocarbyl disulfide in the presence of catalytic amounts of an aluminum phenoxide. Novel and useful (hydrocarbylthio)phenols containing hydrocarbylthio groups in either of both of the meta positions, relative to the hydroxy group, on a phenolic ring can be prepared by this process. (Hydrocarbylthio)phenols containing hydrocarbylthio groups in either of both of the meta positions, relative to the hydroxy group, on a phenolic ring are effective antioxidants for organic material normally susceptible to oxidative deterioration, such as mineral oil.
    Type: Grant
    Filed: November 14, 1983
    Date of Patent: July 22, 1986
    Assignee: Ethyl Corporation
    Inventors: Bonnie G. McKinnie, Paul F. Ranken
  • Process for preparing (hydrocarbylthio)aromatic amines
    Patent number: 4594453
    Abstract: (Hydrocarbylthio)aromatic amines are prepared by reacting an aromatic amine, such as an aminobenzene, with a hydrocarbyl disulfide, such as an alkyl disulfide. The reaction is preferably conducted in the presence of a Lewis acid catalyst, such as aluminum chloride.
    Type: Grant
    Filed: June 11, 1984
    Date of Patent: June 10, 1986
    Assignee: Ethyl Corporation
    Inventors: Paul F. Ranken, Bonnie G. McKinnie
  • 2-amido-3-aminocarboxylic acid esters and process of preparation thereof
    Patent number: 4593118
    Abstract: 2,3-Diaminocarboxylic acid compounds are prepared by (A) nitrosating a .beta.-keto ester to form a 3-keto-2-oximino ester, (B) converting the resultant oxime to a protected 2-amine, (C) reductively aminating the 3-position of the protected 2-amine to form a 2,3-diaminocarboxylic acid ester wherein the 2-amino group is protected, and (D) when desired, treating the 2,3-diaminocarboxylic acid ester to deprotect one or more of the amino and carboxyl groups.
    Type: Grant
    Filed: March 6, 1985
    Date of Patent: June 3, 1986
    Assignee: Ethyl Corporation
    Inventor: Beverly A. Bauer
  • Substituted naphthoic acid process
    Patent number: 4590010
    Abstract: 6-Alkoxy-5-trifluoromethyl-1-naphthoic acids are prepared by (1) cyanating a 6-alkoxytetralone so as to form a 6-alkoxy-1-cyano-3,4-dihydronaphthalene, (2) converting the 6-alkoxy-1-cyano-3,4-dihydronaphthalene to a naphthoic acid precursor selected from a 6-alkoxy-1-cyanonaphthalene and a hydrocarbyl 6-alkoxy-1-naphthoate, (3) halogenating the naphthoic acid precursor to the corresponding 5-halo derivative, (4) trifluoromethylating the 5-halo derivative to replace the 5-halo substituent with a 5-trifluoromethyl group, and (5) hydrolyzing the resultant product to a 6-alkoxy-5-trifluoromethyl-1-naphthoic acid. In a preferred embodiment of the invention, the process is conducted so as to prepare 6-methoxy-5-trifluoromethyl-1-naphthoic acid, which, like the other products, is known to be useful as a pharmaceutical intermediate.
    Type: Grant
    Filed: April 18, 1985
    Date of Patent: May 20, 1986
    Assignee: Ethyl Corporation
    Inventors: Venkataraman Ramachandran, Robert I. Davidson, John R. Maloney
  • Process for preparing alpha arylacrylonitriles
    Patent number: 4590013
    Abstract: An alpha-arylacrylonitrile is prepared by reacting an aryl ketone having a removable hydrogen alpha to the carbonyl group with a cyanide ion source which is free of radicals that would stabilize a cyanohydrin corresponding to the aryl ketone and with a Lewis acid, preferably in the presence of a solvent. In a preferred embodiment, the aryl ketone is a tetralone, the cyanide ion source is hydrogen cyanide, the Lewis acid is aluminum chloride, and the product is a 1-cyano-3,4-dihydronaphthalene.
    Type: Grant
    Filed: May 17, 1985
    Date of Patent: May 20, 1986
    Assignee: Ethyl Corporation
    Inventors: John R. Maloney, Venkataraman Ramachandran
  • Process for preparing alpha-arylacrylonitriles
    Patent number: 4590012
    Abstract: An alpha-arylacrylonitrile is prepared by reacting an aryl ketone having a removable hydrogen alpha to the carbonyl group with an alkali metal cyanide and a Lewis acid other than aluminum chloride, preferably in the presence of a solvent. In a preferred embodiment, the aryl ketone is a tetralone, the cyanide is sodium cyanide, the Lewis acid is boron trifluoride, and the product is a 1-cyano-3,4-dihydronaphthalene.
    Type: Grant
    Filed: May 17, 1985
    Date of Patent: May 20, 1986
    Assignee: Ethyl Corporation
    Inventor: Venkataraman Ramachandran
  • Preparation of substituted benzaldehydes
    Patent number: 4585898
    Abstract: 3-Bromobenzaldehydes are prepared by reacting a benzaldehyde having a free 3-position with bromine chloride in the presence of aluminum chloride and a small amount of dibromomethane.
    Type: Grant
    Filed: December 18, 1984
    Date of Patent: April 29, 1986
    Assignee: Hardwicke Chemical Company
    Inventors: Roland L. Lau, John S. Hudson
  • Nucleophilic displacement process for preparing 2,6-dihydrocarbonyl-4-(nitroaryl)phenol
    Patent number: 4582947
    Abstract: 2,6-Dihydrocarbyl-4-(nitroaryl)phenols are prepared by reacting (1) a nitroaromatic compound bearing a displaceable substituent selected from nitro and phenylsulfonyl on a ring carbon which is adjacent to, or separated by two ring atoms from, the ring carbon bearing the nitro substituent with (2) a 2,6-dihydrocarbylphenol selected from 2,6-di-t-butyl- , 2,6-di-t-amyl-, 2-t-butyl-6-isopropyl-, and 2,6-diphenylphenols having a replaceable hydrogen in the 4-position in an inert solvent and in the presence of a strong base. The preferred nitroaromatic compounds are 1,2- and 1,4-dinitrobenzenes, 1-nitro-2-phenylsulfonylbenzenes, and 1-nitro-4-phenylsulfonylbenzenes; and a preferred phenol is 2,6-di-t-butylphenol.
    Type: Grant
    Filed: February 26, 1985
    Date of Patent: April 15, 1986
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Nucleophilic substitution process combined with additional reaction steps
    Patent number: 4581463
    Abstract: Halonitroarylacetic acid esters are prepared by reacting a halonitroaromatic compound with an alpha,alpha-disubstituted acetic acid ester in an inert solvent and in the presence of a base. The halonitroarylacetic acid esters formed by the process can be readily converted into derivatives, such as pharmaceuticals.
    Type: Grant
    Filed: August 10, 1984
    Date of Patent: April 8, 1986
    Assignee: Ethyl Corporation
    Inventors: G. Patrick Stahly, Barbara C. Stahly
  • Process for preparing alpha-arylacrylonitriles
    Patent number: 4581176
    Abstract: An alpha-arylacrylonitrile is prepared by reacting an aryl ketone having a removable hydrogen alpha to the carbonyl group with a cyanide ion source which is free of radicals that would stabilize a cyanohydrin corresponding to the aryl ketone and with a Lewis acid in the presence of an activating amount of water and/or HCl and preferably in the presence of a solvent. In a preferred embodiment, the aryl ketone is a tetralone, the cyanide ion source is sodium cyanide, the Lewis acid is aluminum chloride, and the product is a 1-cyano-3,4-dihydronaphthalene.
    Type: Grant
    Filed: May 17, 1985
    Date of Patent: April 8, 1986
    Assignee: Ethyl Corporation
    Inventor: Robert I. Davidson
  • Spiroketone process
    Patent number: 4562294
    Abstract: Spiro[5.5]undeca-1,4,8-trien-3-ones are prepared by heating a reaction mixture consisting essentially of a 4-aminomethylphenol, a conjugated diene, and an inert solvent at a temperature of at least about 190.degree. C.
    Type: Grant
    Filed: October 15, 1984
    Date of Patent: December 31, 1985
    Assignee: Ethyl Corporation
    Inventor: Jerry M. Roper
  • Spiroketone process
    Patent number: 4562293
    Abstract: Spiro[5.5]undeca-1,4,8-trien-3-ones are prepared by reacting a phenol having a free p-position with formaldehyde, a nitrogen compound selected from ammonia and primary and secondary amines, and a conjugated diene in an inert solvent at a temperature of at least about 190.degree. C.
    Type: Grant
    Filed: October 15, 1984
    Date of Patent: December 31, 1985
    Assignee: Ethyl Corporation
    Inventor: Jerry M. Roper