Hydrogen Peroxide → 4-Chloro-2,3,5-trimethyl-1-oxidopyridin-1-ium

HRID 2231952Notes

Reaction equation

HRID 2231952 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([CH3:9])[C:3]=1[CH3:10].[OH:11]O>C(O)(=O)C>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][N+:5]([O-:11])=[C:4]([CH3:9])[C:3]=1[CH3:10]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 142036064-Chloro-2,3,5-trimethylpyridine

Product 1

HCID 27791414-Chloro-2,3,5-trimethyl-1-oxidopyridin-1-iumYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

11.3 g (72.8 mmol) 4-chloro-2,3,5-trimethylpyridine was dissolved in 50 ml acetic acid and heated to 60° C. and 6.2 ml (50% H2O2) was added slowly and the temperature maintained for several hours and finally increased to 90° for two hours. The solvent was evaporated and extracted from alkaline water with diethyl ether to remove unreacted starting material. The water phase was saturated with sodium chloride and extracted several times with methylene chloride. The methylene chloride was dried and evaporated to give 10.1 g of product. Yield 83%. M.p. 147°-148° C.

Workup

  1. temperaturethe temperature maintained for several hours
  2. temperaturefinally increased to 90° for two hours
  3. customThe solvent was evaporated
  4. extractionextracted from alkaline water with diethyl ether
  5. customto remove unreacted
  6. extractionextracted several times with methylene chloride
  7. dry with materialThe methylene chloride was dried
  8. customevaporated

Sources & evidence

ORD record
ord-b28c3cc8f7194d5a82ebbc978810ceed
Source dataset
uspto-grants-1988_11
Patent number
US04785113

Reaction notes

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