Water → Ethyl chloronicotinate

HRID 861917Notes

Reaction equation

HRID 861917 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:17](I)[CH3:18].O>CN(C)C=O>[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:17][CH3:18])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 762582-Chloronicotinic acid

Product 1

HCID 2796614Ethyl chloronicotinateYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

25.7 g of 2-chloronicotinic acid was dissolved in 350 ml of dimethylformamide followed by the addition of 23.6 g of potassium carbonate and 15.8 ml of ethyl iodide and the solution was stirred for 18 hours at room temperature. Water was added to the reaction solution followed by extraction with ethyl acetate (200 ml×3). After washing with water and saturated brine, the reaction solution was dried with anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue was purified with silica gel column chromatography (elution solvent: hexane/ethyl acetate=1/1) to obtain 29.7 g of the target compound. Yield: 98%

Workup

  1. extractionfollowed by extraction with ethyl acetate (200 ml×3)
  2. washAfter washing with water and saturated brine
  3. dry with materialthe reaction solution was dried with anhydrous sodium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe residue was purified with silica gel column chromatography (elution solvent: hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-8558bfc1455e484184b050e094420efa
Source dataset
uspto-grants-1998_02
Patent number
US05716958

Reaction notes

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