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

Organic compounds -- part of the class 532-570 series – Organic compounds – Nitriles

Reexamination Certificate

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Reexamination Certificate

active

08049029

ABSTRACT:
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 3wherein R1is NHR3or OR4; R2is CH3or Cl; R3is H, C1-C4alkyl, cyclopropyl, cyclopropylcyclopropyl, cyclopropylmethyl or methylcyclopropyl; R4is H or C1-C4alkyl; Y is Br or Cl; X is NR13or O; n is 0 or 1; and R5, R6, R7, R8, R9, R10, R11, R12and R13are as defined in the disclosure.Also disclosed is a method for preparing a compound of Formula 2 wherein Y is Br and R1is NHR3comprising 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 R14, R15, R16and 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.

REFERENCES:
patent: 6759554 (2004-07-01), Buchwald et al.
patent: 6867298 (2005-03-01), Buchwald et al.
patent: 2004/0138468 (2004-07-01), Buchwald et al.
patent: 2004/067528 (2004-08-01), None
patent: 2006/023783 (2006-03-01), None
patent: 2006/062978 (2006-06-01), None
patent: 2006/068669 (2006-06-01), None
patent: WO 2006062978 (2006-06-01), None
patent: WO 2006068669 (2006-06-01), None
patent: 2008/070158 (2008-06-01), None
Zanon et al., Copper-Catalyzed Domino Halide Exchange-Cyanation of Aryl Bromides, J. Am. Chem. Soc. 2003, 125, pp. 2890-2891.

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