Hydrogen Peroxide → 5-Methoxy-2-methyl-1-oxo-1lambda~5~-pyridine

HRID 1789049Notes

Reaction equation

HRID 1789049 reaction equation
[OH:1]O.[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH3:11])=[N:9][CH:10]=1>C(O)(=O)C>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH3:11])=[N+:9]([O-:1])[CH:10]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 133587775-Methoxy-2-methylpyridine

Product 1

HCID 122140195-Methoxy-2-methyl-1-oxo-1lambda~5~-pyridineYield 77%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

120 g pf 30% strength hydrogen peroxide solution are added dropwise to a solution of 60.9 g of 5-methoxy-2-methylpyridine in 300 ml of glacial acetic acid at 60° C. in the course of 1 hour and the mixture is subsequently stirred for 3 hours. After destruction of excess percompounds by addition of active manganese dioxide, the mixture is filtered, the filtrate is concentrated, the residue is clarified hot in 500 ml of ethyl acetate, the mixture is concentrated again and the residue is distilled under 0.3 mbar. 54 g (77% of theory) of 5-methoxy-2-methylpyridine 1-oxide are obtained as a rapidly solidifying oil (b.p. 130° C.); m.p. 80°-84° C.

Workup

  1. customAfter destruction of excess percompounds
  2. additionby addition of active manganese dioxide
  3. filtrationthe mixture is filtered
  4. concentrationthe filtrate is concentrated
  5. concentrationthe mixture is concentrated again
  6. distillationthe residue is distilled under 0.3 mbar

Sources & evidence

ORD record
ord-0e53d6247c794354adba0fbdbe5f7b4c
Source dataset
uspto-grants-1987_08
Patent number
US04686230

Reaction notes

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