2-Chloro-4-(2,5-difluoro-4-nitrophenoxy)pyridine → Benzenamine, 4-[(2-chloro-4-pyridinyl)oxy]-2,5-difluoro-

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Reaction Steps

In a Parr Shaker flask was combined 2-chloro-4-(2,5-difluoro-4-nitrophenoxy)pyridine (11.68 g, 40.8 mmol) and MeOH (200 ml) under argon. Raney Ni (50% wet, 0.955 g, 8.15 mmol) was added. The argon atmosphere was removed and replaced with hydrogen (10-20 psi) and the reaction mixture shaken under hydrogen for 4 hours. The completed reaction mixture was filtered through a pad of Celite® and the filtrate was concentrated to dryness to provide 4-(2-chloropyridin-4-yloxy)-2,5-difluoroaniline (8.2 g, 72% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.28 (d, J=5.9 Hz, 1H), 7.25 (dd, J=11.2, 7.5 Hz, 1H), 7.02 (dd, J=2.2 Hz, 1H), 6.95 (dd, J=5.8, 2.0 Hz, 1H), 6.74 (dd, J=12.3, 8.3 Hz, 1H), 5.57 (s, 2H); MS (ESI): m/z 257.0 [M+H]+

Provenance & Evidence