Acetic Anhydride → 4-[(3-Bromophenyl)-N-acetylamino]-6,7-dihydroxy-3-quinolinecarbonitrile

Participants

Reaction Steps

A solution of 4-(3-bromophenylamino)-6,7-dihydroxy-3-quinolinecarbonitrile (1.78 g, 5.0 mmol), dimethylaminopyridine (60 mg, 0.50 mmol), 5.0 ml of acetic anhydride, and 10 ml of pyridine was stirred at reflux temperature for 1.5 h and concentrated to dryness. The residue was stirred with 50 ml of methanol, 5 ml of water, and sodium bicarbonate (2.1 g, 25 mmol) at 25° C. for 16 h and concentrated to dryness. The residue was stirred with water containing acetic acid to give pH-4-5, and the resulting solid was filtered off, washed with water, and dried. A solution of the resulting solid in THF was passed through a pad of silica gel; the filtrate was concentrated to give a tan solid; mass spectrum (electrospray, m/e) M-H 396.3, 398.3.

Provenance & Evidence