Dimethylamine → 2-Amino-5-bromo-N,N-dimethylbenzamide

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Reaction Conditions

Reaction Steps

A 350 ml round bottomed pressure tube was charged with 5-bromoisatoic anhydride (15.0 g, 62.0 mmol) and 2 M dimethylamine in tetrahydrofuran (90 ml, 180 mmol). The vial was sealed and heated in an oil bath at 60° C. for 1 hour, then concentrated to dryness. The residue was dissolved in dichloromethane (100 ml). The organic layer was washed with saturated, aqueous sodium bicarbonate solution (25 ml), and water (25 ml), then dried over sodium sulfate and concentrated to obtain a yellow powder. The powder was re-crystallized from ether to obtain 11.8 g (78.6%) of 2-amino-5-bromo-N,N-dimethyl-benzamide. 1H-NMR (250 MHz, CDCl3) δ 7.20 (dd, J=8.5, 2.5 Hz, 1H), 7.10 (d, J=2.5 Hz, 1H), 6.65 (d, J=8.7 Hz, 1H), 5.34 (s, 2H), 2.91 (s, 6H); MS: m/z 243.1, 245.1 (M+H+).

Provenance & Evidence