5-fluoro-N-(3-fluorophenyl)-2-nitroaniline → 4-Fluoro-N2-(3-fluorophenyl)benzene-1,2-diamine

Participants

Reaction Steps

(5-Fluoro-2-nitrophenyl)-(3-fluorophenyl)amine (2.79 g, 11.16 mmol) was dissolved in EtOAc (110 mL) and the flask evacuated and flushed with nitrogen gas. 10% Pd/C (0.3 g) was added and the reaction mixture stirred under an atmosphere of hydrogen gas, at RT overnight. A further amount of 10% Pd/C (0.3 g) was added and the reaction mixture stirred under an atmosphere of hydrogen gas for an further 2 h. The resultant mixture was filtered through Celite® and the filtrate concentrated in vacuo to afford the title compound as a brown oil, which solidified on standing (2.57 g, 100%). 1H NMR (CDCl3, 400 MHz): δ 7.17 (1H, td, J=8.16, 6.58 Hz), 6.94-6.87 (1H, m), 6.76-6.70 (2H, m), 6.62-6.47 (3H, m), 5.35 (1H, s), 3.54 (2H, s)

Provenance & Evidence