Nitric Acid → 2-Chloro-6-methyl-4-nitropyridin-N-oxide

Participants

Reaction Conditions

Reaction Steps

2-Chloro-6-methyl-pyridine 1-oxide (5.0 g, 0.035 mol) was dissolved in concentrated sulfuric acid (20 ml) at 0° C. An ice-cooled mixture of concentrated nitric acid (12 ml) in concentrated sulfuric acid (20 ml) was added dropwise with stirring at 0° C. The cooling bath was removed, stirring was continued for 3 hours at 90° C. The mixture was poured into a mixture of icewater and ethyl acetate and the resulting precipitate was removed by filtration. The phases of the filtrate were separated, the aqueous phase was extracted several times with ethyl acetate, basified with NaOH and extracted again with ethyl acetate. The combined organic phases were dried over magnesium sulfate and the solvent removed under reduced pressure. The residue was combined with the filtered residue above to yield 6.21 g of a yellow solid (0.033 mol, 94%). MS (ESI) m/z=189.0 [M+1]+.

Provenance & Evidence