Pyridine → 4-[(3-Bromophenyl)amino]-6,7-dimethoxyquinoline-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of 3.02 g of 4-[(3-bromophenyl)amino]-6,7-dimethoxy-3-quinolinecarboxamide, 2.43 ml of pyridine, and 22.5 ml of dichloromethane at 0° C. was added 3.18 ml of trifluoroacetic anhydride during 3 min. The reaction mixture was warmed to 25° C., stirred for 60 min, and concentrated. The residue was dissolved in 38 ml of methanol. The resulting solution was treated with 15 ml of 5 N NaOH at 25° C. After 5 m the solution was acidified with carbon dioxide and evaporated free of methanol. The residue was partitioned with dichloromethane-water. The organic layer was washed with water, dried, and evaporated to give a white solid. Recrystallization from ethyl acetate-hexane gave mp 224-228° C.

Provenance & Evidence