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

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+).

1. customA white precipitate was formed immediately
2. temperatureThe mixture was cooled rapidly
3. customthe solid removed by filtration
4. washwashed with EtOH (40 ml)
5. additionwas added
6. temperatureThe mixture was heated
7. temperatureto reflux overnight
8. temperatureThe resulting mixture was cooled to 0°
9. filtrationthe precipitate filtered off
10. washthe solid washed with EtOH (50 ml), water (50 ml) and finally EtOH (50 ml)

ORD record

ord-dcf59d487c4d4fe0ab2557798dee8e08

Source dataset

uspto-grants-2005_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06953798B1