[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8].OO.C(=O)([O-])[OH:12].[Na+]>C(O)(=O)C>[CH3:1][C:2]1[CH:3]=[N+:4]([O-:12])[CH:5]=[CH:6][C:7]=1[CH3:8]Firstly, under an argon gas atmosphere, 27.3 g of 3,4-dimethylpyridine (Aldrich) (255 mmol) in 150 mL acetic acid solution was cooled on ice, and 25 mL of 35% hydrogen peroxide aqueous solution was added thereto, stirred at 75° C. for 3 hours. Then additional 17.5 mL of 35% hydrogen peroxide aqueous solution was added and stirred at 75° C. for 3 hours. The reaction solution was neutralized by adding an aqueous solution of sodium hydrogen carbonate, extracted with methylene dichloride. The extract was dried on salt cake and concentrated to give a solid. The obtained solid was washed with ethyl acetate to give 29.55 g of 3,4-dimethylpyridine-N-oxide (94% yield).
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