Hydrogen Peroxide → 2,3,5-Trimethyl-1-oxidopyridin-1-ium

HRID 2418247Notes

Reaction equation

HRID 2418247 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][N:3]=1.[OH:10]O>C(O)(=O)C>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][N+:3]=1[O-:10]

Participants

4

Reactant 2

HCID 784Hydrogen Peroxide2×HCID 127592,3,5-Trimethylpyridine

Product 1

HCID 104869072,3,5-Trimethyl-1-oxidopyridin-1-iumYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

18 g of 2,3,5-trimethylpyridine [F. Bohlmann, A. Englisch, J. Politt, H. Sander and W. Weise, Chem.Ber. 88, 1831 (1955)] and 17 ml of 30% strength hydrogen peroxide are heated in 80 ml of glacial acetic acid for 2.5 hours at 100° C. After this time additional 10 ml of 30% strength hydrogen peroxide are added and the mixture is kept at 100° C. for a further 8 hours. The mixture is then concentrated to half of its volume in vacuo. If the solution is free of peroxide, the remaining solvent is stripped off in vacuo. The residue is distilled under a high vacuo. 19.2 g (95%) of 2,3,5-trimethylpyridine-N-oxide of b.p. 95°-98° C. (1.3 Pa) are obtained.

Workup

  1. concentrationThe mixture is then concentrated to half of its volume in vacuo
  2. distillationThe residue is distilled under a high vacuo

Sources & evidence

ORD record
ord-60c07bd13dc64f5ca459d47b71d73714
Source dataset
uspto-grants-1984_09
Patent number
US04472409

Reaction notes

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