Hydrochloric Acid → 4-(1-Amino-ethyl)-benzoic acid methyl ester hydrochloride

Participants

Reaction Steps

To a degassed solution of methyl 4-(1-(hydroxyimino)ethyl)benzoate (1.1 g, 5.6 mmol) and 12.0 M of hydrochloric acid in water (0.6 mL, 7.3 mmol) in methanol (50 mL) was added 10% palladium on carbon (0.20 g, 0.18 mmol). The reaction mixture was stirred overnight at room temperature. All insolubles were removed via filtration through celite and subsequent evaporation of the filtrate to dryness afforded the title compound as a white solid (1.12 g, 83%). LC-MS: (FA) ES+ 180; 1H NMR (400 MHz, MeO D) δ 8.09 (d, J=8.4 Hz, 1H), 7.58 (d, J=8.4 Hz, 1H), 4.55 (q, J=6.8 Hz, 1H), 3.91 (s, 3H), 1.65 (d, J=6.9 Hz, 3H).

Provenance & Evidence