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

HRID 703162Notes

Reaction equation

HRID 703162 reaction equation
[OH:1]O.[N:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:4]=1[CH3:11]>C(O)(=O)C>[CH3:11][C:4]1[C:5]([CH3:10])=[CH:6][C:7]([CH3:9])=[CH:8][N+:3]=1[O-:1]

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

Procedure

420 ml of 30% hydrogen peroxide were added dropwise at room temperature to 246.4 g of 2,3,5-collidine and 2400 ml of glacial acetic acid. The solution was stirred at 80° overnight. The reaction mixture was then cooled to 40° , a further 420 ml of 30% hydrogen peroxide were added thereto and the mixture. was heated to 80° for a further 24 hours. After evaporation in vacuo the residue was dissolved in 300 ml of water. whereupon the solution was made basic with concentrated sodium hydroxide solution while cooling, saturated with sodium chloride and extracted three times with 1 1 of methylene chloride. The organic phases were dried over sodium sulfate and evaporated in vacuo. The residue was crystallized from ether/petroleum ether; there was obtained 2,3,5-trimethyl-pyridine 1-oxide of melting point 42-44° .

Workup

  1. temperatureThe reaction mixture was then cooled to 40°
  2. temperaturewas heated to 80° for a further 24 hours
  3. customAfter evaporation in vacuo the residue
  4. dissolutionwas dissolved in 300 ml of water
  5. temperaturewhile cooling, saturated with sodium chloride
  6. extractionextracted three times with 1 1 of methylene chloride
  7. dry with materialThe organic phases were dried over sodium sulfate
  8. customevaporated in vacuo
  9. customThe residue was crystallized from ether/petroleum ether

Sources & evidence

ORD record
ord-c1bc4f19208841c39e9ec25fa710a2c9
Source dataset
uspto-grants-1991_01
Patent number
US04981861

Reaction notes

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