Hydrochloric Acid → 1-(5-Amino-2-methoxyphenyl)ethanone

Participants

Reaction Steps

Hydrochloric acid (6M, 50 ml) was added to a mixture of N-(3-acetyl-4-methoxyphenyl)acetamide (10.34 g, 50 mmol) and ethanol (150 ml) and the mixture was stirred under reflux for 8 hours. The mixture was cooled and the solvent was evaporated under reduced pressure. Water (100 ml) was added and the pH was adjusted to 10.0 with saturated aqueous potassium carbonate. The mixture was extracted with dichloromethane (3×100 ml) and the combined organic fractions were dried (MgSO4) and evaporated under reduced pressure to give 1-(5-amino-2-methoxyphenyl)ethanone as a dark oil (8.16 g, 99%), 1H NMR (CDCl3) δ 7.09 (1H, d, J=2.8 Hz), 6.82 (2H, m), 3.84 (3H, s), and 3.34 (2H, br. s), 2.59 (3H, s). m/e (CI+) 166 (MH+).

Provenance & Evidence