2-Methoxy-1,3-dimethyl-5-nitrobenzene → 4-Methoxy-3,5-dimethylaniline

Participants

Reaction Steps

To a solution of 2-methoxy-1,3-dimethyl-5-nitrobenzene (12 g) in ethanol in a Parr hydrogenation bottle, was added Pd/C (0.24 g, 10%). The mixture was shaken at 50 psi of H2 in the hydrogenator overnight. The reaction mixture was filtered through Celite® and the solvent was removed by evaporation. The crude residue was purified by column chromatography (10% ethyl acetate/hexane), giving 4-methoxy-3,5-dimethylaniline as a light yellow solid (8.2 g). 1H-NMR (300 MHz, CDCl3) δ=6.18 (s, 1H), 3.711 (s, 3H), 2.29 (s, 6H) ppm. MS: m/z 152 (100, M+H)+

Provenance & Evidence