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

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Reaction Steps

2,6-Dimethyl-4-nitroanisole (3, 29 g, 160 mmol), 10% Pd-C (200 mg) and ethanol (300 mL) were placed in a 500-mL Parr hydrogenation flask and hydrogenated at 50 psi for 24 h. The resulting solution was filtered through a silica gel column using ethyl acetate as eluent. Concentration of the solvent and drying under vacuum gave 23.7 g (98% yield) of 4-amino-2,6-dimethylanisole (4) as a brown-colored solid, mp 59°-60° C. (lit.: Bruice, T. C.; Kharasch, N.; Winzler, R. J. J. Org. Chem. 1953, 18, 83; 63° C.).

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