Chloroacetyl chloride → 8-Acetyl-5-(benzyloxy)-2H-benzo[b][1,4]oxazin-3(4H)-one

Participants

Reaction Conditions

Reaction Steps

2-Chloroacetyl chloride (1.77 mL) was added dropwise to a stirred mixture of 1-(3-amino-4-(benzyloxy)-2-hydroxyphenyl)ethanone (5.2 g) and sodium hydrogen carbonate (3.74 g) in DMF (30 mL) and then stirred for a further 2 h. Cesium carbonate (7.90 g) was added and heated at 100° C. for 20 h. The mixture was cooled to ambient temperature, quenched with water (500 mL), extracted with ethyl acetate (2×200 mL), washed with water (3×300 mL) and brine, dried over anhydrous sodium sulfate, filtered and evaporated under vacuum. The solid residue was treated with ether, filtered and dried to afford the subtitled compound as a beige solid (5.7 g). 1H NMR (400 MHz, DMSO-d6) δ 10.33 (s, 1H), 7.55 (m, 2H), 7.39 (m, 2H), 7.34 (d, J=8.8 Hz, 1H), 7.33 (m, 1H), 6.89 (d, J=9.2 Hz, 1H), 5.27 (s, 2H), 4.67 (s, 2H), 3.32 (s, 3H).

Provenance & Evidence