Hydrogen Peroxide → 3,4-Dimethylpyridine 1-oxide

HRID 705399Notes

Reaction equation

HRID 705399 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8].OO.C(=O)([O-])[OH:12].[Na+]>C(O)(=O)C>[CH3:1][C:2]1[CH:3]=[N+:4]([O-:12])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 114173,4-DimethylpyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 3024543,4-Dimethylpyridine 1-oxideYield 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
75 °C

Procedure

Firstly, under an argon gas atmosphere, 27.3 g of 3,4-dimethylpyridine (Aldrich) (255 mmol) in 150 mL acetic acid solution was cooled on ice, and 25 mL of 35% hydrogen peroxide aqueous solution was added thereto, stirred at 75° C. for 3 hours. Then additional 17.5 mL of 35% hydrogen peroxide aqueous solution was added and stirred at 75° C. for 3 hours. The reaction solution was neutralized by adding an aqueous solution of sodium hydrogen carbonate, extracted with methylene dichloride. The extract was dried on salt cake and concentrated to give a solid. The obtained solid was washed with ethyl acetate to give 29.55 g of 3,4-dimethylpyridine-N-oxide (94% yield).

Workup

  1. additionwas added
  2. stirringstirred at 75° C. for 3 hours
  3. extractionextracted with methylene dichloride
  4. customThe extract was dried on salt cake
  5. concentrationconcentrated
  6. customto give a solid
  7. washThe obtained solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-8bbc1abb675749739693587cec480959
Source dataset
uspto-grants-2015_11
Patent number
US09174906B2

Reaction notes

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