Propionitrile → 3-Chloro-5-(trifluoromethyl)pyridine-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

Propionitrile (656 ml), 2,3-dichloro-5-trifluoromethylpyridine (87.5 g) and 4-dimethylaminopyridine (52 g) were heated at reflux for 5 hours under nitrogen. The mixture was cooled and a solution of sodium cyanide (30 g) in water (110 ml) added at 15° C. After stirring at 15° C. for 5 hours the reaction was complete and water (250 ml) added to dissolve the inorganic salts. The organic phase was washed with water followed by extraction with 2N HCl to remove 4-dimethylaminopyridine. Propionitrile was removed by vacuum distillation at 40° C. to give the product, 3-chloro-2-cyano-5-trifluoromethylpyridine in 73 to 84% yield.

Provenance & Evidence