Benzonitrile, 2,5-dimethyl-4-nitro- → 4-Amino-2,5-dimethylbenzonitrile

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Reaction Steps

2,5-Dimethyl-4-nitrobenzonitrile (500 mg, 2.84 mmol; purchased from Salor) was dissolved in ethanol (20 ml), treated with 10% Pd on carbon catalyst (50 mg) and stirred under a hydrogen atmosphere (10 psi, room temperature, 3 hr). The catalyst was removed by filtration and the solvent evaporated to dryness. The resultant mixture was dissolved in CH2Cl2 and washed with HCl (2N, 4×15 ml), aqueous layer was treated with NaHCO3 then extracted repeatedly with CH2Cl2. Solvent was evaporated from the organic layer to give the desired product (brown solid, 350 mg, 84%). 1H NMR (CD3OD) δ 2.10 (s, 3H), 2.30 (s, 3H), 6.60 (s, 1H), 7.20 (s, 1H). LRMS m/z=147.4 (M+1)+. Found C, 72.12, H, 6.86, N, 18.53%; C9H10N2.0.2H2O requires C, 72.16, H, 7.00, N, 18.70%.

Provenance & Evidence