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

HRID 1702138Notes

Reaction equation

HRID 1702138 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° 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 an additional 3 hours. Then the mixture is poured into water and extracted with diethyl ether, and the organic phase is washed and dried over anhydrous sodium sulfate and subsequently concentrated. The product is purified by chromatography on silica gel with n-hexane/ethyl acetate (1:2) to yield 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
  5. customThe product is purified by chromatography on silica gel with n-hexane/ethyl acetate (1:2)

Sources & evidence

ORD record
ord-ada214616f2c4a279fe2d0c4100d5714
Source dataset
uspto-grants-1983_04
Patent number
US04380544

Reaction notes

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