Nitric Acid → 2,6-Lutidine, 4-nitro-, 1-oxide

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Reaction Conditions

Reaction Steps

Lutidine-N-oxide (19 g, 155 mmol) is cooled at 0° C. and a mixture of fuming HNO3 (100%, 37.5 mL) and conc. H2SO4 (95-97%, 52.5 mL), prepared by addition of H2SO4 to HNO3 at 0° C., is added slowly. The mixture is heated at 80° C. for 3 h. The cooled mixture is carefully poured into ice-water (500 mL). A white precipitate forms that is filtered. The precipitate is dissolved in CH2Cl2 (100 mL) and the filtrate is extracted with CH2Cl2 (4×75 mL). The organic extracts are combined with the dissolved precipitate and washed with sat. aq. NaCl (2×75 mL), dried (Na2SO4), filtered and evaporated to provide the title compound.

Provenance & Evidence