[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(OO)(=[O:17])C.C(O)(C)C>C(O)(=O)C.ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][N+:5]([O-:17])=[CH:4][C:3]=1[O:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1A solution of 25 g of 4-methyl-3-phenoxypyridine, [J.Med.Chem., 18, 1 (1975)] in 90 ml of glacial acetic acid is treated with 30 ml of 40% peracetic acid in acetic acid and the mixture is stirred and heated at 60° C. for 12 hours. Two further 10 ml portions of 40% peracetic acid are added and the mixture heated 4 hours at 60° C. 100 ml of isopropanol is added and the mixture is heated at 90° C. for 4 hours. The mixture is stripped at reduced pressure and dissolved in 500 ml of dichloromethane. The organic layer is washed with an excess of 25% sodium hydroxide solution, dried over anhydrous magnesium sulfate, filtered, concentrated, and distilled to yield 4-methyl-3-phenoxypyridine-1-oxide. B.P. 150°-152° C./0.3 mm
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