Hydrochloric Acid → 4-Chloro-2-methyl-1-oxo-1lambda~5~-pyridine

Participants

Reaction Steps

2-methyl-4-nitropyridine 1-oxide (5.0 g, 32 mmol, 1.0 eq) was dissolved in concentrated HCl (80 mL) and refluxed for 3 days. The reaction was cooled and the excess concentrated HCl was removed in vacuo. The viscous oil was neutralized with 10% K2CO3 and extracted with CH2Cl2 (5×). The combined organics were dried (MgSO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 3.49 g (75%) of the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 8.23 (d, J=7.0 Hz, 1H), 7.66 (d, J=3.0 Hz, 1H), 7.40 (dd, J=7.0, 3.0 Hz, 1H), 2.32 (s, 3H); ES-MS [M+1]+: 144.2.

Provenance & Evidence