Ethyl 6-nitroquinoxaline-2-carboxylate → Ethyl 6-aminoquinoxaline-2-carboxylate

Participants

Reaction Steps

To a flask containing compound 7 (2.93 g, 11.9 mmol) in ethanol (500 mL) was added 10% Pd/C (300 mg). The mixture was degassed and stirred under a H2 atmosphere for 3 h 45. The catalyst was removed by filtration through Celite® 545, washed with ethanol (50 mL) and the filtrate was evaporated. The resulting crude product was purified by chromatography (Al2O3, CH2Cl2/EtOH, 99/1, v/v) to afford the title product 8 (1.69 g, 7.79 mmol) as a dark yellow solid. Yield 66%; Rf (Al2O3, CH2Cl2/EtOH, 99/1, v/v) 0.55; mp 181-183° C.; IR (KBr)□ ν 1299, 1487, 1613, 1701, 3202, 3431 □cm−1; 1H NMR (200 MHz, CDCl3) δ 1.49 (t, 3H, J=7 Hz), 4.38 (m, 2H), 4.56 (q, 2H, J=7 Hz), 7.16 (d, 1H, J=2.5 Hz), 7.26 (dd, 1H, J=2.5, 9 Hz), 8.05 (d, 1H, J=9 Hz), 9.35 (s, 1H); MS m/z 217 (M+, 23), 145 (100), 117 (19), 90 (16), 63 (14).

Provenance & Evidence