Phosphorus pentachloride → 2-Chloro-4,6-dimethyl-3-pyridinecarbonitrile

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 3-cyano-4,6-dimethyl-2-hydroxypyridine (4.35 g, 29.39 mmol) and phosphorous pentachloride (6.92 g, 33.21 mmol) is heated to 120° C. The reaction mixture becomes clear and is stirred for an additional 1 hr. It is then poured onto ice/water (250 mL) and allowed to stand for 30 min. The solution is neutralized with sodium bicarbonate (pH 6) and extracted with dichloromethane (400 mL). The separated organic layer is dried, filtered and concentrated to yield 2-chloro-3-cyano-4,6-dimethylpyridine (4.60 g, 94% yield) as a tan solid containing ca 15% impurity. LC/MS: MS m/e=167/169 (M+H); RT 2.98 min; NMR (CDCl3, δ ppm) 7.08 (1H, s), 2.57 (3H, s), 2.55 (3H, s).

Provenance & Evidence