Yield:116296-36-7 28%

Reaction Conditions:

Stage #1: 2,6-dimethyl-4-nitroacetanilidewith acetic acid;zinc in tetrahydrofuran at 0; for 0.5 h;
Stage #2: with sodium hydrogencarbonate in tetrahydrofuran;methanol;water;ethyl acetate;Saturated solution;

Steps:

N-(4-Amino-2,6-dimethyl-phenyl)-acetamide.; Zinc dust (30 g) was added in portions over 10 minutes to JV-(2,6-dimethyl-4-nitro-phenyl)- acetamide (5.09 g) in tetrahydrofuran (200 mL) and acetic acid (60 mL) cooled to 0 0C. The reaction mixture was filtered after 30 minutes through silica (50 g), which was washed with methanol/ethyl acetate (20:80, 100 mL). The organic phase was washed with saturated aqueous sodium bicarbonate (100 mL) and treated with heptane until the title compound precipitated, which was collected, washed with heptane and dried in vacuo to furnish 1.20 g (28% yield) of the title compound as a pale red solid. 1H NMR (500 MHz, DMSO-d6): 1.95 (s, 3H), 1.96 (s, 6H)5 4.82 (s, 2H), 6.23 (s, 2H), 8.79 (s, IH).

References:

WO2006/29623,2006,A1 Location in patent:Page/Page column 54-55