Acetyl chloride → 4-Chloro-2-methyl-1-oxo-1lambda~5~-pyridine

HRID 1196620Notes

Reaction equation

HRID 1196620 reaction equation
[N+]([C:4]1[CH:5]=[C:6]([CH3:11])[N+:7]([O-:10])=[CH:8][CH:9]=1)([O-])=O.C([Cl:15])(=O)C.C([O-])([O-])=O.[K+].[K+]>>[Cl:15][C:4]1[CH:5]=[C:6]([CH3:11])[N+:7]([O-:10])=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 95291Pyridine, 2-methyl-4-nitro-, 1-oxide

Product 1

HCID 122118014-Chloro-2-methyl-1-oxo-1lambda~5~-pyridine

Procedure

15.4 g (0.1 mol) of 4-nitro-2-picoline-N-oxide are added in portions at 0° C. to 75 ml of acetyl chloride. On warming to room temperature, a clear solution results which is added dropwise to ice with stirring. After adding K2CO3, the mixture is extracted several times using dichloromethane and ethyl acetate. After evaporating, the product is purified chromatographically on silica gel. The oil obtained crystallizes on standing, m.p. 37° C.

Workup

  1. customa clear solution results which
  2. additionis added dropwise to ice
  3. extractionthe mixture is extracted several times
  4. customAfter evaporating
  5. customthe product is purified chromatographically on silica gel
  6. customThe oil obtained
  7. customcrystallizes on standing, m.p. 37° C.

Sources & evidence

ORD record
ord-0e9510eff730453db6f28636110286eb
Source dataset
uspto-grants-1992_05
Patent number
US05114955

Reaction notes

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