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

Participants

Reaction Conditions

Reaction Steps

Into a 350 ml round bottomed pressure tube were added 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 the mixture was concentrated to dryness. The residue was dissolved in dichloromethane (100 ml). The organic layer washed with saturated, aqueous sodium bicarbonate solution (25 ml), washed with water (25 ml), dried over sodium sulfate, filtered, 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