Hydrochloric Acid → HCID 67173093, compound

Participants

Reaction Steps

A mixture of methyl(3-nitrophenethyl)sulfane (4.4 g, 22 mmol) and iron powder (3.75 g, 67 mmol) in MeOH was stirred at room temperature, then aqueous HCl (20 g, 36.5%) was added slowly, then the mixture solution was heated to reflux for 3 hours. The solvent was evaporated, and saturated sodium bicarbonate was added, the aqueous layer was extracted with ethyl acetate 3 times. The combined organic phase was washed with brine, dried over sodium sulfate and concentrated to give 3-(2-(methylthio)ethyl)aniline (3.5 g, yield 94%). 1H NMR: 400 MHz CDCl3 δ 7.11-7.07 (m, 1H), 6.63-6.61 (m, 1H), 6.56-6.54 (m, 1H), 3.64 (s, 2H), 2.83-2.71 (m, 4H), 2.13 (s, 3H).

Provenance & Evidence