3-Nitrostyrene → 3-Aminostyrene

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence