2-Propenoic acid, 3-(4-nitrophenyl)- → 3-amino-3-(4-nitrophenyl)propanoic Acid

Participants

Reaction Steps

To a hot solution of sodium ethoxide prepared from sodium (9.33 g, 405 mmol) and EtOH (330 ml) was added a hot solution of hydroxylamine hydrochloride (28.17 g, 405 mmol) in water (18 ml). A white precipitate was formed immediately. The mixture was cooled rapidly and the solid removed by filtration and washed with EtOH (40 ml). The filtrate was then returned to the reaction flask and 4-nitrocinnamic acid (30 g, 155 mmol) was added. The mixture was heated to reflux overnight. The resulting mixture was cooled to 0° and the precipitate filtered off and the solid washed with EtOH (50 ml), water (50 ml) and finally EtOH (50 ml) to give the title compound as a pale yellow solid (16 g, 49%). δH (D2O) 8.31 (2H, d, J 8.7 Hz, ArH), 7.69 (2H, d, J 8.7 Hz, ArH), 4.81 (1H, app. dd. J 7.2, 7.1 CHNH2), 2.94 (1H, dd, J 16.4, 7.7 Hz, CHAHB) and 2.86 (1H, dd, J 16.4 and 6.7 Hz, CHAHB); m/z (ES+, 60V) 211 (MH+).

Provenance & Evidence