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

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

2008-06-23

2011-10-11

Shameem, Golam M M (Department: 1622)

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

Organic compounds

Nitriles

C558S303000, C558S411000, C558S416000

Reexamination Certificate

active

08034968

ABSTRACT:
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 4wherein R1is NHR3or OR4; R2is CH3or Cl; R3is H, C1-C4alkyl, cyclopropyl, cyclopropylcyclopropyl, cyclopropylmethyl or methylcyclopropyl; R4is H or C1-C4alkyl; 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 5wherein R5, R6, R7and 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: 7528260 (2009-05-01), Shapiro et al.
patent: 0384392 (1990-08-01), None
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
Y. Sakakibara et al., “The Cyanation of Aromatic Halides Catalyzed by Nickel(0) Complexes Generated In Situ III”,Bull. Chem. Soc. JP. 2004, vol. 77, pp. 1013-1019.
Y. Sakakibara et al., “The Cyanation of Aromatic Halides Catalyzed by Nickel(0) Complexes Generated In Situ I”,Bull. Chem. Soc. JP. 1988, vol. 61, pp. 1985-1990.
J. Van Soolingen et al., “Nickel-Catalyzed Cyanation of 2- and 3-Bromothiophene”,Synthetic Communications, 1990, vol. 20, pp. 3153-3156.
L. Cassar et al., “Nickel-Catalyzed Cyanation of Aromatic Halides”,Advances in Chemistry, 1974, vol. 132, pp. 252-273.
R. K. Arvela et al., Rapid Easy Cyanation of Aryl Bromides and Chlorides Using Nickel Salts in Conjunction with Microwave Applications:,J. Org. Chem. 2003, vol. 68, pp. 9122-9125.

Affiliated with

Also associated with

Rating

Process for preparing 2-amino-5-cyanobenzoic acid derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for preparing 2-amino-5-cyanobenzoic acid derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for preparing 2-amino-5-cyanobenzoic acid derivatives will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-4264900