Acetic Acid → N-(3-amino-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(2-cyanopropan-2-yl)-N-(4-methyl-3-nitrophenyl)benzamide 4 (27 g, 84 mmol) and CH3COOH (72 mL, 1.3 mol) in THF (300 mL) at rt was added zinc (1.68 mol, 109 g). The temperature was maintained at 20° C. by cooling with an ice bath. The reaction was stirred at 20° C. for 1 hour. After dilution with ether the organic layer was extracted with 1N NaOH solution, water, brine, dried and evaporated to give crude N-(3-amino-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide 5 (24.7 g, 100%). 1H-NMR (400 MHz, CDCl3) 1.77 (s, 6H), 2.15 (s, 3H), 3.68 (br s, 2H). 6.77 (dd, J=7.1 and 1.9 Hz, 1H), 7.02 (d, J=8.0 Hz, 1H), 7.27 (br s, 1H), 7.50 (t, J=8, 1H), 7.69 (m, 1H), 7.75 (m, 2H), 7.96 (m, 1H).

Provenance & Evidence