Ethanol → Ethyl pyridine-4-acetate

HRID 1896247Notes

Reaction equation

HRID 1896247 reaction equation
S(Cl)(Cl)=O.Cl.[N:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[CH:8][CH:7]=1.C(=O)(O)[O-].[Na+].[CH3:21][CH2:22]O>>[N:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([O:15][CH2:21][CH3:22])=[O:14])=[CH:8][CH:7]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 810974-Pyridineacetic acid hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 736321Ethyl pyridine-4-acetateYield 86.2%

Procedure

Thionyl chloride (1.70 ml, 23.0 mmol) was added to a solution of pyridin-4-yl-acetic acid hydrochloride (2.00 g, 11.5 mmol) in EtOH (30 ml) at 0° C. The reaction mixture was heated to reflux for 18 h, then the temperature of the reaction mixture was brought down to room temperature and the volatiles were evaporated in vacuo. The crude reaction mixture was basified with aqueous sodium bicarbonate solution, extracted with ethyl acetate (2×50 ml), washed with water, brine and dried over anhydrous sodium sulfate. After filtration the organic solvent was evaporated and dried to afford 1.50 g (86.2%) of ethyl 2-(pyridin-4-yl)acetate as pale yellow liquid. This was taken as such for the next step.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 18 h
  3. customwas brought down to room temperature
  4. customthe volatiles were evaporated in vacuo
  5. customThe crude reaction mixture
  6. extractionextracted with ethyl acetate (2×50 ml)
  7. washwashed with water, brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationAfter filtration the organic solvent
  10. customwas evaporated
  11. customdried

Sources & evidence

ORD record
ord-756a949850174b54973c5fd6aa0ab070
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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