Ethanol → Ethyl 6-chloronicotinate

HRID 1836833Notes

Reaction equation

HRID 1836833 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.S(=O)(=O)(O)O.[CH2:16](O)[CH3:17]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:16][CH3:17])=[O:7])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 792226-Chloronicotinic acid

Product 1

HCID 2799611Ethyl 6-chloronicotinateYield 84%

Procedure

6-Chloronicotinic acid (1.6 g, 10.0 mmol) was dissolved in ethanol. Concentrated sulfuric acid (0.5 ml) was added to the solution, and the mixture was refluxed overnight. The reaction solution was concentrated under the reduced pressure. The residue was diluted with methylene chloride and was then washed with water, followed by drying over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (development system, n-hexane:ethyl acetate=5:1) to give ethyl 6-chloronicotinate 1.6 g (yield 84%) as a colorless oil.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. concentrationThe reaction solution was concentrated under the reduced pressure
  3. additionThe residue was diluted with methylene chloride
  4. washwas then washed with water
  5. dry with materialby drying over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (development system, n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-887d9a417a434a9f80702ac294c477bf
Source dataset
uspto-grants-2004_08
Patent number
US06777414B1

Reaction notes

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