6-Fluoro-7-(methylamino)-3-(4-nitrophenyl)-2,3-dihydrobenzo[e][1,3]oxazin-4-one → 3-(4-Aminophenyl)-6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-one

Participants

Reaction Steps

To a suspension of 6-fluoro-7-(methylamino)-3-(4-nitrophenyl)-2,3-dihydrobenzo[e][1,3]oxazin-4-one (0.108 g, 0.33 mmol) in ethanol (6 mL) under Ar was added 10% Pd/C (0.04 g, 0.03 mmol Pd). The mixture was hydrogenated under 1 atm H2 overnight, filtered through Celite and concentrated to give 0.096 g (98%) of 3-(4-aminophenyl)-6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-one. RP-HPLC: 1.37 min; ES-MS (M+H)+=288.0; 1H-NMR (MeOH-d4) δ (ppm): 2.8 (s, 3 H), 5.5 (s, 2 H), 6.2 (d, 1 H), 7.2 (d, 2 H), 7.3 (d, 2 H), 7.4 (d, 1 H).

Provenance & Evidence