Phosphorus oxychloride → 4-Chloro-2,6-dimethyl-3-nitropyridine

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Reaction Steps

By the method of Yakugaku Zasshi, 87, 387 (1967), 2,6-dimethyl-3-nitro-4(1H)-pyridone (see part (a)) (11.23 g, 66.8 mmol) and phosphorus oxychloride (57 ml) were heated together at reflux for 1.5 hours. The excess reagent was removed under reduced pressure, and the residue dissolved in dichloromethane (150 ml). This solution was treated with dilute aqueous sodium bicarbonate until the aqueous layer was at pH7, then the organic phase was separated, dried (MgSO4) and concentrated under reduced pressure to give the title compound as a pale yellow solid, (9.8 g, 79%). Caution: this compound is a potential skin irritant.

Provenance & Evidence