Aniline → HCID 10633103, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-fluoro-4-methyl-1-nitrobenzene (1.0 g, 6.45 mmol) in DMSO (3 mL) was purged with a stream of nitrogen prior to addition of phenylamine (1.18 mL, 12.9 mmol) and then stirred in a sealed tube at 100° C. for 20 h. After cooling to RT, the reaction mixture was partitioned between EtOAc (125 mL) and water (150 mL). The organic layer was then washed with water (150 mL×3), followed by brine, then dried (Na2SO4) and concentrated in vacuo affording (5-Methyl-2-nitrophenyl)phenylamine as a red solid (1.5 g, quantitative). 1H NMR (DMSO, 400 MHz): δ 9.40 (1H, s), 8.03 (1H, d, J=8.70 Hz), 7.45-7.39 (2H, m), 7.35-7.30 (2H, m), 7.21 (1H, t, J=7.33 Hz), 6.98 (1H, s), 6.72-6.68 (1H, m), 2.24 (3H, s).

Provenance & Evidence