3-Bromo-o-toluidine → 2-amino-N-(3-bromo-2-methylphenyl)-4-fluorobenzamide

Participants

Reaction Steps

A mixture of 7-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione (5.00 g, 27.6 mmol) and 3-bromo-2-methylaniline (5.14 g, 27.6 mmol) in xylene (50 mL) was heated at reflux for 8 h. The cooled mixture was filtered. The collected solid was washed with 3 times with DCM and the combined filtrates were concentrated. The residue was purified by column chromatography on silica gel (330 g), eluting with EtOAc-hexanes (gradient from 0-45%), to give 2-amino-N-(3-bromo-2-methylphenyl)-4-fluorobenzamide (3.65 g, 41% yield). Mass spectrum m/z 323, 325 (M+H)+. 1H NMR (400 MHz, chloroform-d) δ 7.65 (1 H, d, J=8.14 Hz), 7.45-7.57 (3 H, m), 7.14 (1 H, t, J=8.03 Hz), 6.39-6.50 (2 H, m), 5.80 (2 H, br. s.), 2.43 (3 H, s).

Provenance & Evidence