Aniline → HCID 10609383, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-fluoro-4-methyl-2-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 (200 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 and the resulting residue was purified by column chromatography (Si—PCC, gradient 0-40% DCM in cyclohexane) affording (4-Methyl-2-nitrophenyl)phenylamine as a red oil (1.41 g, 96%). 1H NMR (DMSO, 400 MHz): δ 9.21 (1H, s), 7.94-7.91 (1H, m), 7.43-7.26 (5H, m), 7.19-7.12 (2H, m), 2.27 (3H, s).

Provenance & Evidence