2,4-Difluoronitrobenzene → HCID 62416746, compound

Participants

Reaction Steps

To a solution of 2,4-difluoro-1-nitrobenzene (0.7 mL, 6.3 mmol) in CH3CN (10 mL) were added cyclobutylamine (0.54 mL, 6.3 mmol) and DIPEA (1.1 mL, 6.3 mmol). The reaction mixture was stirred at RT for 18 h then concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% EtOAc in cyclohexane) to afford cyclobutyl-(5-fluoro-2-nitrophenyl)amine as a yellow oil (1.38 g, quantitative). To a solution of the product thus obtained (6.3 mmol) in EtOAc (60 mL) was added 10% Pd/C (150 mg) and the reaction mixture stirred at RT for 18 h under a hydrogen atmosphere. The suspension was filtered through a pad of Celite® and the filtrate concentrated in vacuo to afford the title compound as an orange oil (1.1 g, quantitative). 1H NMR (CDCl3, 300 MHz): δ 6.63-6.56 (1H, m), 6.35-6.19 (2H, m), 3.92-3.78 (1H, m), 3.66-2.91 (2H, m), 2.53-2.36 (2H, m), 1.94-1.73 (4H, m).

Provenance & Evidence