4-(2,5-Difluoro-4-nitrophenyl)morpholine → 2,5-Difluoro-4-(morpholin-4-yl)aniline

Participants

Reaction Steps

A mixture of 4-(2,5-difluoro-4-nitrophenyl)morpholine (11 g, 44 mmol) and 10% Pd—C (50% wet, 1.1 g) in EtOH (150 mL) was hydrogenated for 5 h at room temperature. The reaction mixture was filtered by celite, and the filtrate was concentrated under reduced pressure. The residue was recrystallized from iPr2O/AcOEt to give the title compound (8.6 g, 91% yield) as a pale red powder: 1H NMR (300 MHz, DMSO-d6): δ ppm 2.66-2.95 (4H, m), 3.56-3.83 (4H, m), 5.00 (2H, s), 6.55 (1H, dd, J=13.8, 8.5 Hz), 6.77 (1H, dd, J=12.8, 8.3 Hz). LC-MS (ESI) m/z 215 [M+H]+.

Provenance & Evidence