2-Hydroxyquinoline → 6-(Chloroacetyl)quinolin-2(1H)-one

Participants

Reaction Steps

To a solution containing 467 g of chloroacetyl chloride in 400 ml of dichloromethan, 735 g of aluminium chloride was added by 1/3 each at a temperature below 30° C. with stirring condition. Next 200 g of carbostyril was added thereto at the same temperature under stirring condition. The reaction mixture was refluxed for 6 hours, then the reaction mixture was poured into a mixture of ice-concentrated hydrochloric acid and the crystals formed were collected by filtration. The crystals were washed with methanol, then with hot-methanol to obtain 153 g of 6-chloroacetylcarbostyril. The mother liquor was concentrated to dryness, and the residue obtained was purified by a silica gel column chromatography, then recrystallized from methanol to obtain 35.41 g of 8-chloroacetylcarbostyril in the form of light yellow crystals.

Provenance & Evidence