Phosphorus oxychloride → 4-Chloro-5,7-dimethoxyquinoline

Participants

Reaction Steps

5,7-dimethoxy-1H-quinolin-4-one (300 mg, 1.4 mmol) in POCl3 (5 mL) was heated to reflux for 15 h. The reaction mixture was cooled to rt and poured into ice-water. The mixture was then basified to pH 7 with NaHCO3 and stirred overnight. The solid was filtered and washed with water and dried to give 4-chloro-5,7-dimethoxyquinoline. LCMS m/z=224 (M+1); 1H NMR (CDCl3) δ: 8.56 (d, 1H, J=4.4 Hz), 7.23 (d, 1H, J=4.4 Hz), 7.05 (s, 1H), 6.58 (s, 1H), 3.93 (s, 6H).

Provenance & Evidence