Hydrogen Peroxide → HCID 12811121, compound

HRID 1155712Notes

Reaction equation

HRID 1155712 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[CH:3]=1.[OH:17]O>[C].[Pd].C(O)(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][N+:5]([O-:17])=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=2)[CH:3]=1

Participants

5

Reactant 2

HCID 784Hydrogen Peroxide2×HCID 12811120HCID 12811120, compound

Product 1

HCID 12811121HCID 12811121, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 4-methyl-2-(4-nitrophenyl)pyridine (25.8 g), acetic acid (130 ml) and 30% hydrogen peroxide (27.5 ml) is agitated at 75°-85° C. for 17 hours. To the mixture is added 10% palladium-carbon in order to decompose excess amount of hydrogen peroxide, and then the palladium-carbon is removed by filtration. The filtrate is concentrated, and the concentrated solution is made alkaline with potassium carbonate and extracted with ethyl acetate. The extract is washed with water and dried, and ethyl acetate is distilled off to give 4-methyl-2-(4-nitrophenyl)pyridine N-oxide (26.6 g). M.P. 158°-160° C.

Workup

  1. customthe palladium-carbon is removed by filtration
  2. concentrationThe filtrate is concentrated
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with water
  5. customdried
  6. distillationethyl acetate is distilled off

Sources & evidence

ORD record
ord-404ac176dc3446cdbc4ec27985ad21c4
Source dataset
uspto-grants-1982_06
Patent number
US04332809

Reaction notes

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