Dimethylformamide → 1-[6-(Chloromethyl)pyridin-2-yl]ethanone

HRID 2379806Notes

Reaction equation

HRID 2379806 reaction equation
P(Cl)(Cl)([Cl:3])=O.[C:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15]O)[N:10]=1)(=[O:8])[CH3:7].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[C:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][Cl:3])[N:10]=1)(=[O:8])[CH3:7]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 103294471-(6-(Hydroxymethyl)pyridin-2-yl)ethanone

Product 1

HCID 118194451-[6-(Chloromethyl)pyridin-2-yl]ethanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Phosphorus oxychloride (7.8 ml) was dropwise added to a mixture of 2-acetyl-6-hydroxymethylpyridine (10.0 g) and N,N-dimethylformamide (15.4 ml) in ethyl acetate (100 ml) under ice-cooling with stirring and the mixture was stirred at the same temperature for 3 hours. The reaction mixture was added to water and adjusted to pH 7.5 with potassium carbonate. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated to give 2-acetyl-6-chloromethylpyridine (10.85 g) as an oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at the same temperature for 3 hours
  3. washThe separated organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-b49227bd87f64e7ba28744faa948c3c7
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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