5-Fluoro-N-isopropyl-2-nitroaniline → 5-fluoro-N1-(propan-2-yl)benzene-1,2-diamine

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Reaction Steps

(5-Fluoro-2-nitrophenyl)isopropylamine (2.1 g, 12.6 mmol) was dissolved in EtOAc (60 mL) and the flask evacuated and flushed with nitrogen gas, prior to the addition of 10% Pd/C (0.21 g). The mixture was stirred under an atmosphere of hydrogen gas overnight. A further amount of 10% Pd/C (0.21 g) was added and the mixture was stirred under an atmosphere of hydrogen for a further 3 h. A further amount of 10% Pd/C (0.21 g) was added and the mixture stirred under an atmosphere of hydrogen for a further 2 h. The resultant mixture was filtered through Celite® under an atmosphere of nitrogen and the filtrate concentrated in vacuo to afford the title compound as a dark red oil (1.5 g, 88%). 1H NMR (CDCl3, 400 MHz): δ 6.62 (1H, dd, J=8.34, 5.72 Hz), 6.36 (1H, dd, J=11.17, 2.77 Hz), 6.28 (1H, td, J=8.43, 2.75 Hz), 3.61-3.47 (1H, m), 1.24 (6H, d, J=6.27 Hz)

Provenance & Evidence