4-Methylpyridine → 1-pyridin-4-ylbutan-2-one

HRID 2119054Notes

Reaction equation

HRID 2119054 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[CH3:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1>ClCCl>[CH2:2]([C:1]([CH2:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)=[O:4])[CH3:3]

Participants

4

Reactant 2

HCID 79634-MethylpyridineHCID 62324Propionyl chloride

Product 1

HCID 2382991-pyridin-4-ylbutan-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

19.8 g of propionyl chloride dissolved in 20 ml of dichloromethane was added dropwise over 1 hour to 10 gm of 4-methylpyridine dissolved in 50 ml dichloromethane and maintained below 10° C. After addition, the reaction was brought to ambient temperature, stirred for 8 hours, then brought to reflux for 1 hour. The reaction mixture was quenched into saturated sodium carbonate solution, the organic layer separated and the solvent removed under reduced pressure. The residual 4-methylpyridine was removed by azeotropic distillation under reduced pressure with toluene. Ethanol was added and the mixture refluxed for 6 hours. The solvent was removed under reduced pressure to give 4.45 g of good (4-pyridinylmethyl) ethyl ketone.

Workup

  1. temperaturemaintained below 10° C
  2. additionAfter addition
  3. customwas brought to ambient temperature
  4. temperatureto reflux for 1 hour
  5. customThe reaction mixture was quenched into saturated sodium carbonate solution
  6. customthe organic layer separated
  7. customthe solvent removed under reduced pressure
  8. customThe residual 4-methylpyridine was removed by azeotropic distillation under reduced pressure with toluene
  9. additionEthanol was added
  10. temperaturethe mixture refluxed for 6 hours
  11. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-09f404d9ab39435e84d0a5a95874bf9a
Source dataset
uspto-grants-1987_07
Patent number
US04681944

Reaction notes

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