Phosphorus oxychloride → 2-Chloro-6-ethylnicotinonitrile

Participants

Reaction Steps

A mixture of 3-cyano-6-ethyl-2(1H)-pyridone (36.2 g, 0.24 mol) and phosphorus oxychloride (250 ml) was heated under reflux for 2 hours. The reaction solution was concentrated under a reduced pressure, and the resulting residue was mixed with toluene and concentrated under a reduced pressure. The thus obtained residue was diluted with chloroform and washed with 1 N sodium hydroxide aqueous solution. The aqueous layer was extracted with chloroform, and the chloroform layers were combined and dried over anhydrous magnesium sulfate. After removing magnesium sulfate by filtration, the filtrate was concentrated under a reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 2-chloro-3-cyano-6-ethylpyridine (19.6 g, 49%) as an oily material.

Provenance & Evidence