Nitric Acid → Pyridine, 2,5-dimethyl-4-nitro-, 1-oxide

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Reaction Conditions

Reaction Steps

To a nitrating mixture of sulphuric acid (24 mL) and nitric acid (12 mL) cooled to 0° C. was added 2,5-dimethyl-1-oxido-pyridin-1-ium (CAS: 4986-05-4) (8.4 g, 68.21 mmol). The solution was allowed to warm to room temperature and stirred over 30 mins then heated to 110° C. and stirred over 5 hrs. The reaction mixture was cooled and poured onto ice. The aqueous solution was made basic with solid sodium carbonate, giving a precipitate. The aqueous was extracted into DCM (3x), and the combined extracts were dried over magnesium sulphate, filtered and evaporated to yield a yellow solid, 2,5-dimethyl-4-nitro-1-oxido-pyridin-1-ium (D135) (9.8 g, 58.3 mmol, 85.4% yield);

Provenance & Evidence