2,3-Dimethyl-4-nitrophenol → 4-Hydroxyxylidine

Participants

Reaction Steps

A mixture of 2,3-dimethyl-4-nitrophenol (2 g, 1.2 mmol) and Pd(C) (10%) (1.83 g) in EtOH (80 mL) was stirred at room temperature under H2 atmosphere for 5 hours. The crude mixture was then filtered using celite and washed with DCM. After evaporating the solvent, the title compound (1.60 g, 97%) was obtained as a brown powder. 1H-NMR (6, ppm, DMSO-d6): 1.94 (s, 3H, HMe), 2.01 (s, 3H, HMe), 4.06 (s, 2H, NH2), 6.32 (d, 1H, Harom 6, J6-5=8.1 Hz), 6.40 (d, 1H, Harom 5, J6-5=8.1 Hz), 6.61 (s, 1H, Harom 2), 8.10 (broad s, 1H, OH).

Provenance & Evidence