Sulfuric Acid → 2,3,5-Trimethylpyridine

HRID 2231949Notes

Reaction equation

HRID 2231949 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[C:6](Cl)[N:5]=[C:4]([CH3:10])[C:3]=1[CH3:11].OS(O)(=O)=O>C(O)C.[Zn]>[CH3:10][C:4]1[C:3]([CH3:11])=[CH:2][C:7]([CH3:8])=[CH:6][N:5]=1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 27791392,4-Dichloro-3,5,6-trimethylpyridine

Product 1

HCID 127592,3,5-Trimethylpyridine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

3,8 g (20 mmoles) of 4.6-dichloro-2,3,5-trimethylpyridine are dissolved in a small amount of ethanol and treated with 5 g of zinc powder. After addition of 10 ml of 2 N H2SO4, the mixture is refluxed for 1 hour. After cooling and filtering the solution is treated with NaOH to adjust a pH of 6. The precipitated zinc salts are removed by filtration and the filtrate is extracted three times with petrol ether. After drying and evaporation 2.0 g (83%) of 2,3,5-trimethylpyridine are obtained.

Workup

  1. temperaturethe mixture is refluxed for 1 hour
  2. temperatureAfter cooling
  3. filtrationfiltering the solution
  4. additionis treated with NaOH
  5. customThe precipitated zinc salts are removed by filtration
  6. extractionthe filtrate is extracted three times with petrol ether
  7. customAfter drying
  8. customevaporation 2.0 g (83%) of 2,3,5-trimethylpyridine
  9. customare obtained

Sources & evidence

ORD record
ord-34cdf6932df9494598878de3cecc58af
Source dataset
uspto-grants-1988_11
Patent number
US04785113

Reaction notes

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