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

(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)

1. customthe flask evacuated
2. customflushed with nitrogen gas
3. additionto the addition of 10% Pd/C (0.21 g)
4. additionA further amount of 10% Pd/C (0.21 g) was added
5. stirringthe mixture was stirred under an atmosphere of hydrogen for a further 3 h
6. additionA further amount of 10% Pd/C (0.21 g) was added
7. stirringthe mixture stirred under an atmosphere of hydrogen for a further 2 h
8. filtrationThe resultant mixture was filtered through Celite® under an atmosphere of nitrogen
9. concentrationthe filtrate concentrated in vacuo

ORD record

ord-73b2812f470f42f6a48bc9aaa69b0457

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08653089B2