Hydrochloric Acid → 1-(2-Methylpyridin-4-yl)ethan-1-one

Participants

Reaction Conditions

Reaction Steps

A solution of 3.5 g. (29.7 mmoles) of 2-methyl-4-cyanopyridine in 20 ml. of dry ether was added dropwise to a cooled (5° C.) solution of 20 ml. of 3.0 M methyl magnesium bromide in ether. After addition was complete the mixture was allowed to warm to room temperature and stirred for 18 hours. The reaction mixture was cooled to 5° C. and the excess Grignard reagent decomposed by the addition of water. The mixture was acidified with 6 N hydrochloric acid and the aqueous phase was separated. The ether phase was again extracted with 30 ml. of 1 N hydrochloric acid and the combined aqueous extracts were warmed on a steam bath for one hour. The aqueous solution was cooled, made basic with solid sodium bicarbonate and extracted with (3×100 ml.) ether. The combined ether extracts were dried and evaporated to give 2.1 g. (53%) of a yellow oil. b.p. 50°-53° C. (0.3 torr).

Provenance & Evidence