Phosphorus pentachloride → 2-Chloro-5,6-dimethylpyridine-3-carbonitrile

Participants

Reaction Steps

An intimate mixture of 3-cyano-5,6-dimethyl-2-hydroxypyridine (42 g) and phosphorus pentachloride (81 g) was heated at 140°-160° for 2 hours. Phosphoryl chloride was removed by distillation under reduced pressure and icewater (500 g) was added to the residue. The mixture was adjusted to pH 7 with aqueous sodium hydroxide and extracted with ether. The ether extracts were evaporated to an oil which was crystallised from ether/petroleum ether (b.p. 60°-80°) to give 2-chloro-3-cyano-5,6-dimethylpyridine (25.3 g) m.p. 83°-87°.

Provenance & Evidence