4-(2-(1-Methylpyrrolidin-2-yl)ethyl)-7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one → 7-Amino-4-(2-(1-methylpyrrolidin-2-yl)ethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

Participants

Reaction Steps

A solution of 4-(2-(1-methylpyrrolidin-2-yl)ethyl)-7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (0.49 g, 1.604 mmol) in dry ethanol (5 mL) was treated with Pd—C (˜0.05 g) and purged with hydrogen gas. The flask was evacuated and purged twice with hydrogen gas. The reaction stirred at room temperature under hydrogen atmosphere (balloon pressure) for 2 hours. The reaction was filtered through a Celite bed and washed with methanol (3×10 mL). The combined organic layers were evaporated to obtain the crude title compound (0.44 g, quantitative) as a solid. 1H NMR (DMSO-d6) δ 1.39-1.51 (m, 2H), 1.56-1.66 (m, 2H), 1.76-2.06 (m, 4H), 2.16 (s, 3H), 2.88-2.94 (m, 1H), 3.74-3.86 (m, 2H), 4.46 (s, 2H), 5.01 (s, 2H), 6.22 (d, 1H, J=2.4 Hz), 6.26 (dd, 1H, J=2.1, 8.4 Hz), 6.82 (d, 1H, J=8.4 Hz); ESI-MS (m/z, %): 276 (MH+, 100).

Provenance & Evidence