Sodium Hydroxide → 3-(2-quinoxalinyl)aniline

Participants

Reaction Steps

A solution of 2-(3-nitrophenyl)quinoxaline (9.4 g, 37.4 mmol), SnCl2.H2O (28 g, 13.48 mmol) in CHCl3 (95 mL) was heated to 90° C. for 15 minutes, cooled to room temperature, added to ice water (190 mL), and basified to pH 10 with 50% aqueous NaOH, adding ice as necessary to maintain the temperature below 10° C. The mixture was extracted with ethyl acetate (500 mL), and the organic phase was filtered through a Celite pad, which was washed once with ethyl acetate (150 mL). The combined organics phases were washed with brine and dried, and then solvent was evaporated in vacuo. The resulting solid was recrystallized from toluene to afford (3-quinoxalin-2-ylphenyl)amine (5.6 g, 68% yield). LCMS calculated for C14H11N3 (M+H): 222.26. found 222. 1H-NMR (400 MHz, DMSO-d6) δH: 9.42 (1H, s), 8.11-8.00 (2H, m), 7.94-7.75 (2H, m), 7.55 (1H, s), 7.42 (1H, d, J=7 Hz), 7.22 (1H, m), 6.72 (1H, m), 5.42 (2H, br. s).

Provenance & Evidence