2,2,2-Trifluoroethanol → 2-(2,2,2-Trifluoroethoxy)pyridine-4-carboxylic acid

HRID 1838251Notes

Reaction equation

HRID 1838251 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].CC(C)([O-])C.[K+].[F:17][C:18]([F:22])([F:21])[CH2:19][OH:20]>>[F:17][C:18]([F:22])([F:21])[CH2:19][O:20][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 2369852-Chloroisonicotinic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 187533112-(2,2,2-Trifluoroethoxy)pyridine-4-carboxylic acid

Conditions

Temperature
170 °C

Procedure

A mixture consisting of 7.5 g of 2-chloroisonicotinic acid, 16 g of potassium tert-butoxide and 100 ml of 2,2,2-trifluoroethanol was stirred at 170° C. for 5 days in a sealed tube. After evaporation of the solvent, the residue was mixed with water and 4 N hydrochloric acid and extracted with chloroform. The solvent was washed with water, dried over anhydrous magnesium sulfate and then concentrated, and the thus formed crystals were washed with hexane to obtain 7.7 g of the title compound.

Workup

  1. customAfter evaporation of the solvent
  2. additionthe residue was mixed with water and 4 N hydrochloric acid
  3. extractionextracted with chloroform
  4. washThe solvent was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. washthe thus formed crystals were washed with hexane

Sources & evidence

ORD record
ord-7b939a769c724bb99c9326d1fb3eea1f
Source dataset
uspto-grants-2004_01
Patent number
US06673799B1

Reaction notes

Loading…