US 2010/0305330 A1Published application

Process for preparing 2-alkyl-3-halo-6-nitrilpyridine and its carboxylic acid and ester derivatives

AssigneeSynergetica Changzhou Chemical Company

InventorsHeng E. Michael Su, Yizu Wu, Chunming Wu, Haiyan Li, Lee Alan DeWitt

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Abstract

A process for preparing 2-alkyl-3-halo-6-nitrilpyridine and its carboxylic acid and ester derivatives by reacting 2-alkyl-3-halo-pyridine N-oxide with dimethyl sulfate, followed by reacting the adduct with alkaline cyanide to obtain the target molecule is disclosed. Further treatment of the nitrile with base to obtain the corresponding acid, and esterification are described as well. The process was scaled up to multi-kilogram level that provided satisfactory output.

Claims4

Dependent claims

A process to prepare 2-alkyl-3-halo-6-cyanopyridine and 2-alkyl 3-halopyridine-6-carboxylic acid and esters of 2-alkyl-3-halopyridine-6-carboxylic acid comprised of the following steps:

(a) preparation of N-Oxide of 2-alkyl-3-halo-pyridine with peracetic acid,
(b) adding dimethyl sulfate to form 1-methoxy-2-alkyl-3-halo-pyridinium methyl sulfate,
(c) reacting the adduct 1-methoxy-2-alkyl-3-halo-pyridinium methyl sulfate with alkaline cyanide to form the 2-alkyl-3-halo-6-nitrilpyridine,
(d) hydrolysis of the 2-alkyl-3-halo-6-nitrilpyridine with base to form the corresponding 2-alkyl-3-halopyridine 6-carboxylic acid
(e) esterification of the 2-alkyl-3-halopyridine 6-carboxylic acid to yield the corresponding 2-alkyl-3-halopyridine 6-carboxylic acid ester.

2 more elements

Dependencies are inferred from the claim text.