Ammonium Hydroxide → 2-Amino-5-methoxybenzamide

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6-methoxy-2H-3,1-benzoxazine-2,4(1H)-dione (3.0 g, 16 mmol, Trans World Chemicals) was treated directly with 27% aqueous ammonium hydroxide. After one hour the organic phase was diluted with ethyl acetate, washed twice with aqueous sodium bicarbonate and saturated aqueous sodium chloride, and dried over sodium sulfate. Filtration and removal of the residual solvent gave 2-amino-5-(methyloxy)benzamide as a white solid (1.42 g, 53% Yield);. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.63 (s, 3 H), 6.07 (s, 2 H), 6.60 (d, J=8.97 Hz, 1 H), 6.79 (dd, J=8.79, 2.93 Hz, 1 H), 7.03 (s, 1 H), 7.06 (d, J=2.93 Hz, 1 H), 7.71 (s, 1 H).

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