Hydrochloric Acid → 2-Amino-4-methoxyphenol hydrochloride

Participants

Reaction Steps

A 1 L round bottom 3-neck flask equipped with a magnetic stir bar was charged with 4-methoxy-2-nitrophenol (10.0 g, 59.0 mmol) and 10% Pd/C (1 g, 10% by weight) under argon. Ethyl acetate (200 mL) was then added very slowly to the mixture under argon. The mixture was stirred vigorously at room temperature for several minutes before 1.8 mL of concentrated hydrochoric acid was added. The argon was evacuated from the flask under reduced pressure and the flask was then charged with 1 atm of hydrogen gas and stirred for 18 hours at room temperature before its progress was checked by HPLC (Eclipse XDB-C18, 4.6×250 mm, 5 micron, 1-99% CH3CN/H2O with 0.1% trifluoroacetic acid). The chromatogram indicated that all of the starting material (Rt=5.9 min) was consumed and a new single peak had formed (Rt=2.3 min). The reaction was filtered through 10 g plug of Celite. The organic filtrate was then concentrated by rotary evaporation to give 2-amino-4-(methyloxy)phenol as the HCl salt (6.62 g, 38 mmol, 64%) in the form of a brown amorphous solid. MS (ES) m/e 140 [M+H]+.

Provenance & Evidence