3-Cyanopyridine → Nicotinonitrile 1-oxide

HRID 1441112Notes

Reaction equation

HRID 1441112 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].[OH:9]O>C(O)(=O)C>[C:1]([C:3]1[CH:4]=[N+:5]([O-:9])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 793-CyanopyridineHCID 784Hydrogen Peroxide

Product 1

HCID 84686Nicotinonitrile 1-oxideYield 58.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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.

Workup

  1. temperaturethe mixture is heated
  2. stirringwith stirring, to 100° C. for 2 hours
  3. customThe solvent is cautiously removed by evaporation
  4. additionthe beige solid is treated with 25 ml of ethanol
  5. temperaturecooled
  6. filtrationfiltered
  7. customThe residue is dried at 35° C. under vacuum

Sources & evidence

ORD record
ord-504f83d541d34b368e0a98688b726a96
Source dataset
uspto-grants-1996_03
Patent number
US05502196

Reaction notes

Loading…