HCID 54077828, compound → 6-bromo-3-methyl-3,4-dihydro-1H-quinoxalin-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(5-bromo-2-nitrophenyl)-alanine (22 g, 76 mmol) in acetic acid (300 ml) was added iron powder (10 g, 180 mmol), and the mixture was stirred for 2 hours at 90° C. The reaction mixture was cooled and filtered, and the acetic acid was evaporated. The remaining slurry was extracted with methylene chloride (3×200 ml). The combined extracts were combined, dried over magnesium sulfate, filtered, and evaporated to afford 6-bromo-3-methyl-3,4-dihydro-1H-quinoxalin-2-one (9.4 g, 51%). A sample was recrystallized from ethanol: m.p. 133-135° C. 1H-NMR (DMSO-d6) δ 1.23 (d, J=6.81 Hz, 3H), 3.80 (q, J=6.81 Hz, 1H), 6.27 (bs, 1H), 6.63 (d, J=8.35 Hz, 1H), 6.72 (dd, J=8.35, 1.76 Hz, 1H), 6.80 (d, J=1.76 Hz, 1H), 10.29 (s, 1H).

Provenance & Evidence