3-Nitrostyrene → 3-Aminostyrene

Temperature

70 °C

To a solution of the above 3-ethenylnitrobenzene (10 g) in acetic acid (30 ml) was added zinc powder (10 g) and the mixture heated to 70° C. with stirring for two hours, then cooled to room temperature and filtered. Ethyl acetate (300 ml) was added to the filtrate, followed by 1M sodium hydroxide until pH 10. The organic layer was separated, washed with water (100 ml), brine (100 ml) and dried over magnesium sulphate. The solvent was removed under reduced pressure to give the crude product, which was purified by column chromatography to give 3-ethenylaniline (4.9 g), δ (60 MHz, CDCl3) 3.60 (2H, bs, NH2), 5.1, 5.2, 5.5 and 5.8 (3H, 4d, CH2 and CH) and 6.3 to 7.3 (4H, m, ArH).

1. temperaturecooled to room temperature
2. filtrationfiltered
3. additionEthyl acetate (300 ml) was added to the filtrate
4. customThe organic layer was separated
5. washwashed with water (100 ml), brine (100 ml)
6. dry with materialdried over magnesium sulphate
7. customThe solvent was removed under reduced pressure
8. customto give the crude product, which
9. customwas purified by column chromatography

ORD record

ord-c610710507894e4791d62c2e4012b9c9

Source dataset

uspto-grants-1993_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05270309