N,N-Dimethylaniline → 6-Chloro-1-cycloprop yl-carbonyl-4-oxo-1,2,3,4-tetrahydroquinoline

Participants

Reaction Steps

A solution of cyclopropyl-carbonyl chloride (2.09 g) in chloroform (5 ml) was added dropwise to a solution of 6-chloro-4-oxo-1,2,3,4-tetrahydroquinoline (1.815 g), N,N-dimethylaniline (2.42 g), and 4-dimethylaminopyridine (0.488 g) in chloroform (15 ml) with stirring and ice cooling over a period of 10 minutes. After being stirred overnight at ambient temperature, the mixture was washed successively with 10% hydrochloric acid, water, aqueous sodium bicarbonate, and water, dried over magnesium sulfate, and evaporated in vacuo. The residual solid was washed with diethyl ether and dried to give 6-chloro-1-cyclopropyl-carbonyl-4-oxo-1,2,3,4-tetrahydroquinoline (2.14 g).

Provenance & Evidence