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

HRID 1817284Notes

Reaction equation

HRID 1817284 reaction equation
[N:1]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[CH3:9].[OH:10]O>C(O)(=O)C>[CH3:9][C:2]1[C:3]([CH3:8])=[CH:4][C:5]([CH3:7])=[CH:6][N+:1]=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-ium

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred mixture of 2,3,5-collidine (10 g, 82.5 mmol) and glacial acetic acid (40 mL) was added hydrogen peroxide (30% solution, 20 mL, dropwise) at 65° C. The bath was heated to 90° C. for 1 hour, cooled to 65° C. and additional hydrogen peroxide (30% solution, 10 mL, dropwise) was added. The reaction mixture was heated at 90° C. until completion and cooled to ambient temperature. The solvent was removed under reduced pressure and the crude residue was used directly in the next step.

Workup

  1. customat 65° C
  2. temperaturecooled to 65° C.
  3. temperatureThe reaction mixture was heated at 90° C. until completion
  4. temperaturecooled to ambient temperature
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c2b6496393d2457b93b900e33b7b931f
Source dataset
uspto-grants-2009_10
Patent number
US07598273B2

Reaction notes

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