Water → 2-(2,4-Dichlorophenyl)-1-(3-pyridyl)-1-propanone

HRID 637297Notes

Reaction equation

HRID 637297 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])=[O:8])[CH:2]=1.[H-].[Na+].[CH3:20]I.O>CN(C)C=O>[Cl:17][C:11]1[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:10]=1[CH:9]([CH3:20])[C:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 136712392,4-Dichlorobenzyl 3-pyridyl ketone

Product 1

HCID 140744312-(2,4-Dichlorophenyl)-1-(3-pyridyl)-1-propanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

28 g of 2,4-dichlorobenzyl 3-pyridyl ketone are dissolved in 800 ml of dimethylformamide and treated portionwise at 0° C. with 5.5 g of sodium hydride (50% dispersion in oil). After 2 hours at room temperature 14.9 g of methyl iodide are added and the mixture is stirred at room temperature for a further 3 hours. The mixture is then poured into water and extracted with diethyl ether. The organic phase is washed, dried over anhydrous sodium sulfate and subsequently concentrated. By chromatography on silica gel with n-hexane/ethyl acetate (1:2) there is obtained 2-(2,4-dichlorophenyl)-1-(3-pyridyl)-1-propanone as an oil.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic phase is washed
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationsubsequently concentrated

Sources & evidence

ORD record
ord-6a911e637a3b465ab76bd0d4a991664b
Source dataset
uspto-grants-1985_12
Patent number
US04556661

Reaction notes

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