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

Participants

Reaction Steps

A solution of 7-nitro-4-(2-(pyrrolidin-1-yl)ethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one (0.46 g, 1.579 mmol) in dry ethanol (5 mL) was treated with Pd—C (˜0.05 g) and purged with hydrogen gas. The reaction was stirred under hydrogen atmosphere (balloon pressure) for 4 hours. The reaction was filtered through a Celite bed and washed with methanol (3×10 mL). The combined organic layers were evaporated and dried under vacuum to obtain the crude title compound (0.4 g, 97%) as a solid. 1H NMR (DMSO-d6) δ 1.61-1.70 (m, 4H), 2.44-2.56 (m, 6H, merged with DMSO-d6), 3.90 (t, 2H, J=7.2 Hz), 4.47 (s, 2H), 5.01 (s, 2H), 6.22 (d, 1H, J=2.4 Hz), 6.25 (dd, 1H, J=2.4, 8.2 Hz), 6.84 (d, 1H, J=8.7 Hz); ESI-MS (m/z, %): 262 (MH+, 100), 191 (44).

Provenance & Evidence