Trichloroacetyl chloride → 2-(Chloromethyl)-3-methylpyridine

HRID 979840Notes

Reaction equation

HRID 979840 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N+:3]=1[O-].[Cl:10]C(Cl)(Cl)C(Cl)=O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Cl:10][CH2:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 3840573Pyridine, 2,3-dimethyl-, 1-oxide

Product 1

HCID 130586822-(Chloromethyl)-3-methylpyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 15 g of 2,3-dimethylpyridine 1-oxide in 75 ml of chloroform was boiled at reflux and treated as rapidly as possible with 37 ml of trichloroacetyl chloride (the acid chloride was added through the reflux condenser). The reaction mixture was heated under reflux for 2.5 hours, subsequently poured into a mixture of ice and sodium bicarbonate and the resulting solution was washed several times with methylene chloride. The organic phase was dried with sodium sulfate, filtered and concentrated. The residue was chromatographed on silica gel with methylene chloride, the medium pressure flash chromatography method being used and the pressure being produced with nitrogen gas. The 2-chloromethyl-3-methylpyridine obtained was processed directly.

Workup

  1. temperatureat reflux
  2. additionwas added through the reflux condenser)
  3. temperatureThe reaction mixture was heated
  4. temperatureunder reflux for 2.5 hours
  5. washthe resulting solution was washed several times with methylene chloride
  6. dry with materialThe organic phase was dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was chromatographed on silica gel with methylene chloride
  10. customthe pressure being produced with nitrogen gas

Sources & evidence

ORD record
ord-19699fb55c7442b18693304c6f764e66
Source dataset
uspto-grants-1987_01
Patent number
US04634710

Reaction notes

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