1-(5-chloro-2-Methoxyphenyl)ethanaMine synthesis

Yield:35253-21-5 40%

Reaction Conditions:

Stage #1: 2-methoxy-5-chloroacetophenonewith formic acid;formamide at 170; for 20 h;
Stage #2: with hydrogenchloride;water in water; for 30 h;Heating / reflux;
Stage #3: with sodium hydroxide in water; pH=9;

Steps:

9

1 -(5-Chloro-2-methoxyphenyl)ethanamine:; l-(5-Chloro-2-methoxyphenyl)ethanone (6.7 g, 36.3 mmol) and formic acid (1.74 g, 27.7 mmol) were heated in formamide (10 mL) at 170 ⁰C for 20 h. The mixture was cooled to EPO room temperature, diluted with water and extracted with benzene. After removal of benzene by rotary evaporation the crude mixture was heated under reflux conditions in 3 M HCl for 3O h. After cooling, the reaction was added to ether and extracted. The aqueous layer was basified with NaOH to pH 9 and extracted with dichloromethane. The dichloromethane was evaporated to collect the title compound (2.7 g, 40 %). ¹H NMR (400 MHz, CDC13): δ 7.39 (d, IH), 7.26 (q, IH), 6.81 (d, IH), 4.62 (m, IH), 3.84 (s, 3H), 1.69 (d, 3H).

References:

WO2006/81332,2006,A1 Location in patent:Page/Page column 48-49