102-28-3

122-28-1

102-28-3

m-Nitroacetanilide (1 g, 5.66 mmol) was dissolved in 100 mL of methanol and a catalytic amount of 10% palladium/activated charcoal (~0.015 g) was added. The reaction mixture was cooled via an ice bath and sodium borohydride (1 g, 26.43 mmol) was added in batches. Subsequently, the mixture was stirred vigorously for 1 hour. The reaction process was monitored by thin layer chromatography (TLC) using toluene-acetone (5:2, v/v) as unfolding agent. Upon completion of the reaction, the product was purified by silica gel column chromatography with toluene-acetone (5:2, v/v) as eluent. A white solid product was obtained in 75% yield with a melting point of 86-88 °C. Elemental analysis (C8H10N2O, Mr=150.18) Calculated values: C 63.98%, H 6.71%, N 18.65%; measured values: C 63.76%, H 6.50%, N 18.53%.1H NMR (400 MHz, DMSO-d6) δ: 9.58 (s, 1H, NH), 6.92 (t, 1H, H-2, J = 2.00 Hz), 6.88 (t, 1H, H-4, J = 8.00 Hz), 6.64 (dd, 1H, H-6, J1 = 0.80 Hz, J2 = 8.00 Hz), 6.23 (dd, 1H, H-5, J1 = 1.60 Hz, J2 = 8.00 Hz), 5.00 (bs, 2H, NH2), 1.99 (s, 3H , CH3-CO).13C NMR (100 MHz, DMSO-d6) δ: 167.85 (C=O), 148.85 (C1), 139.85 (C3), 128.75 (C4), 109.04 (C5), 106.93 (C6), 104.67 (C2), 23.98 (CH3-CO).