3-Cyanopyridine → Nicotinonitrile 1-oxide

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Reaction Steps

5.21 g of 3-cyanopyridine are completely dissolved in 50 ml of glacial acetic acid at 40° C., with stirring. Then 9.8 ml of a 30% aqueous solution of H2O2 are added and the mixture is heated, with stirring, to 100° C. for 2 hours. Thin-layer chromatography shows that the reaction is complete. The solvent is cautiously removed by evaporation and the beige solid is treated with 25 ml of ethanol, cooled and and filtered. The residue is dried at 35° C. under vacuum, affording 3.5 g (58.3% of theory) of 3-cyanopyridine-N-oxide as a white solid with a melting point of 172°-174° C.

Provenance & Evidence