Pyridine → 5-nitro-1-phenyl-1H-pyridin-2-one

Participants

Reaction Steps

[Ref. Mederski, W. W. K. R., et al. Tetrahedron, 1999, 55, 12757-12770.] To a solution of 2-hydroxy-5-nitropyridine (1.07 g, 7.64 mmol) in dry methylene chloride (50 mL) were added phenylboronic acid (1.86 g, 15.3 mmol), cupric acetate (1.71 g, 9.41 mmol), pyridine (1.2 mL, 15.3 mmol), triethylamine (2.1 mL, 15.3 mmol) and activated 4 Å molecular sieves (2 g). The resulting mixture was stirred in air at rt for 2 d. The mixture was then filtered through celite and washed with methylene chloride. The crude material was purified by silica gel chromatography, eluting with CH2Cl2:EtOAc (85:15) to give the title compound as a white solid. LC-MS (ES, Pos.): 217 [MH+], and 1H NMR (CDCl3, 400 MHz): δ=6.67 (d, J=10.1 Hz, 1H), 7.39-7.42 (m, 2H), 7.53-7.58 (m, 3H), 8.17 (dd, J=10.1, 3.1 Hz, 1H), 8.67 (d, J=3.1 Hz, 1H).

Provenance & Evidence