Benzoyl chloride → 1-Phenyl-2-(4-pyridinyl)ethanone

HRID 2119055Notes

Reaction equation

HRID 2119055 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1>ClCCl>[N:14]1[CH:15]=[CH:16][C:11]([CH2:10][C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:8])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 79634-Methylpyridine

Product 1

HCID 2871041-Phenyl-2-(4-pyridinyl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
10 °C

Procedure

30.2 g of benzoyl chloride dissolved in 30 cc of dichloromethane was added dropwise over 1 hour to 10 g of 4-methylpyridine dissolved in 60 cc dichloromethane and maintained at 10° C. during the addition. The reaction was brought to room temperature and stirred 16 hours. The reaction was brought to reflux for 1 hour, then cooled and quenched into saturated sodium carbonate solution. The organic layer was separated, solvent removed under reduced pressure and alcohol added. The mixture was refluxed 16 hours, then the solvent removed under reduced pressure. The residue was taken up in dichloromethane and washed two times with 3N HCl. The organic layer was separated and the aqueous acid layer first neutralized, then saturated with sodium carbonate. Dichloromethane extraction of the product, solvent removal and azeotropic removal of excess unreacted 4-methylpyridine using toluene gave 4.85 g of desired product.

Workup

  1. customwas brought to room temperature
  2. temperatureto reflux for 1 hour
  3. temperaturecooled
  4. customquenched into saturated sodium carbonate solution
  5. customThe organic layer was separated
  6. customsolvent removed under reduced pressure and alcohol
  7. additionadded
  8. temperatureThe mixture was refluxed 16 hours
  9. customthe solvent removed under reduced pressure
  10. washwashed two times with 3N HCl
  11. customThe organic layer was separated
  12. extractionDichloromethane extraction of the product, solvent removal and azeotropic removal of excess unreacted 4-methylpyridine

Sources & evidence

ORD record
ord-c2b6abe349964f1dbef7eb56e38bd7ae
Source dataset
uspto-grants-1987_07
Patent number
US04681944

Reaction notes

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