Thionyl Chloride → Ethyl 6-(chloromethyl)nicotinate

HRID 1030513Notes

Reaction equation

HRID 1030513 reaction equation
O[CH2:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]=1.S(Cl)([Cl:16])=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Cl:16][CH2:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 15045504Ethyl 6-(hydroxymethyl)pyridine-3-carboxylate

Product 1

HCID 15045505Ethyl 6-(chloromethyl)nicotinateYield 90.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 10.5 g of ethyl 6-hydroxymethylnicotinate in chloroform (100 ml) was cooled to 0° C., and 8.28 g of thionyl chloride was added dropwise to the solution. The mixture was stirred at 0° C. for 2 hours, an aqueous solution of sodium hydrogencarbonate was added, and the mixture was extracted with dichloromethane. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexene/ethyl acetate=6/1) to obtain 10.52 g of ethyl 6-chloromethylnicotinate.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (n-hexene/ethyl acetate=6/1)

Sources & evidence

ORD record
ord-c261d04a19c4419686e6e6b2aa1e8fca
Source dataset
uspto-grants-1992_04
Patent number
US05106859

Reaction notes

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