E.i. Dupont De Nemours and Company

University of California

E. I. Du Pont Nemours and Co.

Fmc Corporation

Gary David Annis

Rafael Shapiro

Stephen Frederick McCann

Thomas Martin Stevenson

George Philip Lahm

Brenton Todd Smith

Thomas Paul Selby

Stephen Ernest Jacobson

Donald J Dumas

Morris P Rorer

Wenming Zhang

Chi-Ping Tseng

Albert Loren Casalnuovo

Kanu Maganbhai Patel

Bruce Lawrence Finkelstein

William E Barnette

Joerg Bruening

Richard James Brown

Keith Dumont Wing

William Francis Smith, Iii

King-Mo Sun

Victor E Amoo

Tom Paul Selby

Philip Osborne Moss

David Raymond Forney

George Chih-Shu Chiang

Robert W March, Jr

Stephen Frederick Mccann

Disclosed is a method for preparing a compound of Formula 1 wherein Q and Z are as defined in the disclosure comprising distilling water from a mixture comprising a compound of Formula 2, a compound of Formula 3, a base comprising at least one compound selected from the group consisting of alkaline earth metal hydroxides of Formula 4 wherein M is Ca, Sr or Ba, alkali metal carbonates of Formula 4a wherein Mis Li, Na or K, 1,5-diazabicyclo[4.3.0]non-5-ene and 1,8-diazabicyclo[5.4.0]undec-7-ene, and an aprotic solvent capable of forming a low-boiling azeotrope with water. Also disclosed is a method for preparing a compound of Formula 2 comprising (1) forming a reaction mixture comprising a Grignard reagent derived from contacting a compound of Formula 5 wherein X is Cl, Br or I with magnesium metal or an alkylmagnesium halide in the presence of an ethereal solvent, and then (2) contacting the reaction mixture with a compound of Formula 6 wherein Y is ORor NRR, and R, Rand Rare as defined in the disclosure. Further disclosed is a method for preparing a compound of Formula 7 wherein Q and Z are as defined in the disclosure, using a compound of Formula 1 characterized by preparing the compound of Formula 1 by the method disclosed above or using a compound of Formula 1 prepared by the method disclosed above. 

Method for preparing 3-trifluoromethyl chalcones

Disclosed is a method for preparing a compound of Formula 1 wherein Q and Z are as defined in the disclosure comprising distilling water from a mixture comprising a compound of Formula 2, a compound of Formula 3, a base comprising at least one compound selected from the group consisting of alkaline earth metal hydroxides of Formula 4 wherein M is Ca, Sr or Ba, alkali metal carbonates of Formula 4a wherein Mis Li, Na or K, 1,5-diazabicyclo[4.3.0]non-5-ene and 1,8-diazabicyclo[5.4.0]undec-7-ene, and an aprotic solvent capable of forming a low-boiling azeotrope with water.  Also disclosed is a method for preparing a compound of Formula 2 comprising (1) forming a reaction mixture comprising a Grignard reagent derived from contacting a compound of Formula 5 wherein X is Cl, Br or I with magnesium metal or an alkylmagnesium halide in the presence of an ethereal solvent, and then (2) contacting the reaction mixture with a compound of Formula 6 wherein Y is ORor NRR, and R, Rand Rare as defined in the disclosure.  Further disclosed is a method for preparing a compound of Formula 7 wherein Q and Z are as defined in the disclosure, using a compound of Formula 1 characterized by preparing the compound of Formula 1 by the method disclosed above or using a compound of Formula 1 prepared by the method disclosed above. 

Disclosed is a method for preparing a compound of Formula 1 wherein with hydroxylamine in the presence of a base. The present invention also relates to novel compounds of Formula 2, useful as starting materials for the aforedescribed method.

Method for preparing 5-haloalkyl-4, 5-dihydroisoxazole derivatives

Method for preparing 5-haloalkyl-4,5-dihydroisoxazole derivatives

Disclosed is a method for preparing a compound of Formula 1 comprising contacting a compound of Formula 2 with a metal cyanide reagent, a copper(I) salt reagent, an iodide salt reagent and at least one compound of Formula 3 wherein Ris NHRor OR; Ris CHor Cl; Ris H, C-Calkyl, cyclopropyl, cyclopropylcyclopropyl, cyclopropylmethyl or methylcyclopropyl; Ris H or C-Calkyl; Y is Br or Cl; X is NRor O; n is 0 or 1; and R, R, R, R, R, R, R, Rand Rare as defined in the disclosure. Also disclosed is a method for preparing a compound of Formula 2 wherein Y is Br and Ris NHRcomprising introducing a gas containing bromine into a liquid containing a compound of Formula 4, and further disclosed is a method for preparing a compound of Formula 5 wherein R, R, Rand Z are as defined in the disclosure using a compound of Formula 1 characterized by preparing the compound of Formula 1 by the method disclosed above. 

Process for preparing 2-amino-5-cyanobenzoic acid derivatives

Disclosed is a method for preparing a compound of Formula 1 comprising (1) contacting a compound of Formula 2, with (2) at least one alkali metal cyanide and (3) at least one compound of Formula 4 wherein Ris NHRor OR; Ris CHor Cl; Ris H, C-Calkyl, cyclopropyl, cyclopropylcyclopropyl, cyclopropylmethyl or methylcyclopropyl; Ris H or C-Calkyl; and X is Br, Cl or I. Also disclosed is a method for preparing a compound of Formula 4 comprising contacting a mixture of (i) at least one compound of Formula 9 and (ii) at least one metal reducing agent with (iii) dichlorobis(triphenylphosphine)nickel, and further disclosed is a method for removing nickel impurities from a mixture thereof with compounds of Formula 1 comprising contacting the mixture with oxygen in the presence of an aqueous cyanide solution, and additionally disclosed is a method for preparing a compound of Formula 5 wherein R, R, Rand Z are as defined in the disclosure, using a compound of Formula 1, characterized by preparing the compound of Formula 1 by the method disclosed above.

Disclosed a method for preparing a compound of Formula 1, wherein Ris cyclopropyl, 4-chlorophenyl or 4-bromophenyl; and Ris C-Calkyl; comprising contacting a compound of Formula 2 with a persulfate oxidant in the presence of a strong sulfur- or phosphorus-containing mineral acid and an oxidation resistant solvent. Also disclosed are methods for preparing the compound of Formula 2 from a compound of Formula 5 as well as compounds of Formula 6 and salts thereof, 

Method for preparing substituted pyrimidines

This invention provides compounds of Formula I, methods for their preparation and use for preparing compounds of Formula II  This invention also discloses preparation of compounds of Formula III  This invention also pertains to certain compounds of Formula 4 and 6 used to prepare compounds of Formula I. 

[object Object]

A method is disclosed for preparing a 2-substituted-5-oxo-3-pyrazolidinecarboxylate compound of Formula I The method comprises contacting a succinic acid derivative of the formula ROC(O)C(H)(X)C(R)(R)C(O)Y (i.e. Formula II) wherein X and Y are leaving groups and L, R, Rand Rare as defined in the disclosure, with a substituted hydrazine of the formula LNHNH(i.e. Formula III) in the presence of a suitable acid scavenger and solvent. Also disclosed is the preparation of compounds of Formula IV wherein X, R, R, R, R, R, and n are as defined in the disclosure. Also disclosed is a composition comprising on a weight basis about 20 to 99% of the compound of Formula II wherein R, R, R, R, Rand Rare as defined in the disclosure; X is Cl, Br or I; and Y is F, Cl, Br or I; provided that when Rand Rare each H, and X and Y are each Cl then Ris other than benzyl and when Rand Rare each phenyl, and X and Y are each Cl, then Ris other than methyl or ethyl. Also disclosed is a crystalline composition comprising at least about 90% by weight of the compound of the formula ROC(O)C(H)(X)C(R)(R)COH (i.e. Formula VI) wherein Rand Rare H, X is Br and Ris methyl.

Preparation and use of 2-substituted-5-oxo-3-pyrazolidinecarboxylates

This invention relates to a method for preparing a 3-halo-4,5-dihydro-1H-pyrazole compound of Formula I comprising contacting with HXa different 4,5-dihydro-1H-pyrazole compound of Formula II wherein Xis halogen and L, R, k and Xare as defined in the disclosure. This invention also discloses preparation of compounds of Formula III wherein X, R, R, R, R, Rand n are as defined in the disclosure.

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Landenberg, PA, United States of America

Gary David Annis