N-Cyclohexyl-5-fluoro-2-nitroaniline synthesis

Yield:1270967-29-7 92%

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine in acetonitrile at 20;

Steps:

Cyclohexyl-(5-fluoro-2-nitrophenyl)amine 2,4-Difluoronitrobenzene (2.00 g, 12.57 mmol) was dissolved in acetonitrile (20 mL) and cyclohexylamine (1.25 g, 12.57 mmol) and DIPEA (2.2 mL, 12.57 mmol) added. The reaction mixture was stirred at RT overnight. The resultant mixture was concentrated in vacuo to afford a bright yellow gum. This was purified by column chromatography (silica gel, gradient 0-10% EtOAc in cyclohexane) to afford the title compound as a bright yellow oil (2.4 g, 92%). ¹H NMR (CDCl₃, 400 MHz): δ 8.20 (1H, dd, J=9.50, 6.22 Hz), 6.49 (1H, dd, J=11.75, 2.62 Hz), 6.31 (1H, ddd, J=9.51, 7.26, 2.61 Hz), 3.47-3.33 (1H, m), 2.11-1.98 (2H, m), 1.85-1.77 (2H, m), 1.72-1.60 (1H, m), 1.48-1.26 (5H, m)

References:

US2012/202785,2012,A1 Location in patent:Page/Page column 211