1,2-Dichloroethane → HCID 14851958, compound

Participants

Reaction Steps

A solution of 6 g of 3,4-dihydro-2(1H)-quinolinone in 50 ml of formic acid and 50 ml of conc. hydrochloric acid was added to 75 ml of 1,2-dichloroethane which had been saturated with chlorine. The mixture was stirred over ice for 30 minutes. Chlorine was introduced for 5 minutes and stirring in the cold was continued for 2 hours. It was then poured onto ice, was made basic with ammonium hydroxide and was extracted with methylene chloride. The extracts were dried and evaporated and the residue was chromatographed over 300 g of silica gel using 8% (v/v) of ethyl acetate in methylene chloride. Crystallization of the combined clean fractions from ether gave colorless crystals of 6,8-dichloro-3,4-dihydro-2(1H) quinolinone with m.p. 145°-146°.

Provenance & Evidence