Acetic Acid → 2-(3-Chloro-4-methoxyphenyl)ethan-1-amine

Participants

Reaction Steps

Methoxyphenethyl amine (39.4 g, 0.261 mol) was dissolved in water (300 mL) and concentrated HCl(22mL). To this solution was added chlorine gas (20.3 g, 0.287 mol) in glacial acetic acid (300 mL) over a 15 minute period while maintaining the temperature below 35° C. After standing for ten minutes, the volatiles were removed in vacuo and the dark solid residue was dissolved in absolute ethanol (100 mL) and allowed to crystallize at -10° C. The collected precipitate was dissolved in a mixture of saturated sodium bicarbonate (400 mL) and dichloromethane (400 mL). The organic layer was separated and dried over anhydrous sodium sulfate. It was condensed on a rotorevaporator to afford a dark oil which was distilled (115°-116° C./1.75 mm Hg) to give 12.8 g(26.4%) of a clear oil. 1R (neat) 3600-3310 (br,NH2), 1600, 1500, 1250 and 1060 cm-1 ; 1H NMR(CDCl3)δ,d 7.36-6.71 (m, 3H, ArH), 3.85 (S, 3H, OCH3), 3.15-2.48 (m, 4H, (CH2)2), 1.12(S, 2H, NH2).

Provenance & Evidence