O-Phenylenediamine → 2-(3-nitrophenyl)quinoxaline

Participants

Reaction Steps

A mixture of 2-bromo-1-(3-nitrophenyl)ethanone (20.5 g, 84 mmol), 1,2-phenylenediamine (8.6 g, 80 mmol) and sodium acetate (12.2 g, 90 mmol) in ethanol (EtOH) (250 mL) was heated at reflux for 5 hrs. The reaction mixture was cooled to room temperature, filtered, washed with EtOH and water, and dried to afford 2-(3-nitrophenyl)quinoxaline (11.9 g, 59% yield). LCMS calculated for C14H9N3O2 (M+H): 252.25. found 252; (M+H+MeCN): 293.10. found 293. 1H-NMR (400 MHz, DMSO-d6) δH: 9.62 (1H, s), 9.12 (1H, m), 8.81 (1H, m), 7.42 (1H, m), 8.30-8.10 (2H, m), 8.00-7.82 (3H, m).

Provenance & Evidence