Quinoline → 2-chloro-3-nitro-6-(trifluoromethyl)pyridine

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Reaction Conditions

Reaction Steps

To phosphorous oxychloride (11 ml, 117 mmol) was added quinoline (8.4 ml, 70 mmol) followed by 3-nitro-6-trifluoromethyl-2(1H)-pyridone (24.0 g, 115 mmol), and the resulting solution heated at 140° C. for 18 h. The solution was then cooled to 100° C., when water (50 ml) was carefully added. After cooling to room temperature, saturated sodium bicarbonate (200 ml) was added and the mixture extracted with ethyl acetate (2×200 ml). The extracts were dried (MgSO4) and concentrated, and the residue purified by silica chromatography to give the product as a brown oil (22.7 g, 0.1 mol, 87% yield).

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