US 2011/0034695 A1 · PROCESS FOR PREPARING 2-AMINO-5-CYANOBENZOIC ACID DERIVATIVES

Abstract

Disclosed is a method for preparing a compound of Formula 1 comprising contacting a compound of Formula 2 with at least one alkali metal cyanide of Formula 3 and a compound of Formula 4. wherein R1 is NHR3 or OR4; R2 is CH3 or Cl; R3 is H, C1-C4 alkyl, cyclopropyl, cyclopropylcyclopropyl, cyclopropylmethyl or methylcyclopropyl; R4 is H or C1-C4 alkyl; X is Br, Cl or I; and R5, R6, R7, R8, R9 and R10 are as defined in the disclosure. Also disclosed is a method for preparing a compound of Formula 4 wherein R9 and R10 together are a cycloalkadiene bidentate ligand, comprising contacting a compound of Formula 5 wherein Y is Cl, Br or I, with a cycloalkadiene bidentate ligand, at least one metal reducing agent and a nitrile solvent. Also disclosed is a method for preparing a compound of Formula 1 comprising preparing a compound of Formula 4 by contacting a compound of Formula 5 with a cycloalkadiene bidentate ligand and at least one metal reducing agent, and then contacting the reaction mixture comprising the compound of Formula 4 with a compound of Formula 2 and at least one alkali metal cyanide of Formula 3; and further disclosed is a method for preparing a compound of Formula 6 wherein R15, R16, R17 and Z are as defined in the disclosure using a compound of Formula 1, characterized by preparing the compound of Formula 1 by a method disclosed above.

Claims27

Dependent claims

A method for preparing a compound of Formula 1

wherein
R1 is NHR3 or OR4;
R2 is CH3 or Cl;
R3 is H, C1-C4 alkyl, cyclopropyl, cyclopropylcyclopropyl, cyclopropylmethyl or methylcyclopropyl;
and
R4 is H or C1-C4 alkyl;
comprising contacting (1) a compound of Formula 2
wherein each X is independently Br, Cl or I;
with (2) at least one compound of Formula 3
M1CN 3
wherein M1 is sodium, potassium, cesium or rubidium;
and (3) a compound of Formula 4
wherein
R5 is a phenyl ring optionally substituted with up to 5 substituents independently selected from R11;
R6 is a phenyl ring or a naphthalenyl ring system, each ring or ring system optionally substituted with up to 5 substituents independently selected from R12;
R7 is a phenyl ring optionally substituted with up to 5 substituents independently selected from R13;
R8 is a phenyl ring or a naphthalenyl ring system, each ring or ring system optionally substituted with up to 5 substituents independently selected from R14;
each R9 and R10 is independently a displaceable ligand;
or
R9 and R10 together are a bidentate, displaceable ligand;
and
each R11, R12, R13 and R14 is independently fluorine, C1-C6 alkyl, C1-C6 fluoroalkyl, C1-C6 alkoxy, C1-C6 fluoroalkoxy, C1-C6 alkylamino or C2-C6 dialkylamino;
provided that when X is Cl, then R2 is methyl.

20 more elements

Dependencies are inferred from the claim text.

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

Life of this patent

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

Life of this patent

Abstract

Claims27