Ammonia → 4-Carbamoyl-3-nitrobenzoic acid

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Reaction Steps

4-(Methoxycarbonyl)-3-nitrobenzoic acid (100 g, 0.44 mol) was taken into concentrated aqueous ammonia (37w %, 500 mL), and the resulting yellow solution was allowed to stir at room temperature over 12 hours. The solution was then reduced in volume to approximately 300 mL by rotary evaporation, and the solution was acidified to pH 2 by portion-wise addition of concentrated aqueous hydrochloric acid. The thick precipitate was collected by filtration and dried in vacuo to afford 4-(aminocarbonyl)-3-nitrobenzoic acid (51 g, 60% yield). 1H-NMR (d6-DMSO): 8.42 (d, 1H), 8.27 (dd, 1H), 8.26 (br s, 1H), 7.86 (br s, 1H), 7.76 (d, 1H).

Provenance & Evidence