2,4-Dichlorobenzyl chloride → 2,4-Dichlorobenzyl 3-pyridyl ketone

HRID 1702137Notes

Reaction equation

HRID 1702137 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH2:4]Cl.[OH-:11].[Na+].[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19](N2CCOCC2)C#N)[CH:14]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([CH2:4][C:3]2[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:2]=2[Cl:1])=[O:11])[CH:14]=1

Participants

5

Reactant 3

HCID 72122,4-Dichlorobenzyl chlorideHCID 14798Sodium HydroxideHCID 303572(Morpholin-4-yl)(pyridin-3-yl)acetonitrile

Product 1

HCID 136712392,4-Dichlorobenzyl 3-pyridyl ketone

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

125 g of 2,4-dichlorobenzyl chloride are added at room temperature to a mixture of 700 g of 50% sodium hydroxide, 23 g of tetrabutylammonium iodide and 130 g of α-(3-pyridyl)-4-morpholineacetonitrile. After 2 hours the mixture is extracted with diethyl ether. After evaporation of the ether, the crude product, α-(2,4-dichlorobenzyl)-α-(3-pyridyl)-4-morpholineacetonitrile (m.p. 130°-132°), remains behind. The crude product is taken up in 300 ml of concentrated hydrochloric acid and the solution is heated to reflux temperature for 12 hours. The reaction mixture is made basic and extracted with ethyl acetate, and the organic phase is washed, dried over anhydrous sodium sulfate and concentrated. Crystallization from ethyl acetate/n-hexane yields 2,4-dichlorobenzyl 3-pyridyl ketone of melting point 78°-79°.

Workup

  1. extractionAfter 2 hours the mixture is extracted with diethyl ether
  2. customAfter evaporation of the ether
  3. temperaturethe solution is heated
  4. temperatureto reflux temperature for 12 hours
  5. extractionextracted with ethyl acetate
  6. washthe organic phase is washed
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customCrystallization from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-000df4629a4a4ef2be7ce7eccf4c81e0
Source dataset
uspto-grants-1983_04
Patent number
US04380544

Reaction notes

Loading…