Water → 3-Chloro-5-(2,2-difluoro-ethoxy)-pyridine-2-carboxylic acid

HRID 1752497Notes

Reaction equation

HRID 1752497 reaction equation
[Cl:1][C:2]1[C:3]([C:13]#N)=[N:4][CH:5]=[C:6]([O:8][CH2:9][CH:10]([F:12])[F:11])[CH:7]=1.[OH-:15].[Na+].[OH2:17]>O1CCOCC1>[Cl:1][C:2]1[C:3]([C:13]([OH:17])=[O:15])=[N:4][CH:5]=[C:6]([O:8][CH2:9][CH:10]([F:12])[F:11])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 866891672-Pyridinecarbonitrile, 3-chloro-5-(2,2-difluoroethoxy)-

Product 1

HCID 866891683-Chloro-5-(2,2-difluoro-ethoxy)-pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 3-Chloro-5-(2,2-difluoro-ethoxy)-pyridine-2-carbonitrile (0.202 g, 0.878 mmol) in dioxane (4 ml) was added 4N NaOH (2.2 ml, 8.8 mmol) and the resulting reaction mixture was stirred for 28 h at 85° C. The reaction mixture was diluted with water and extracted with EtOAc. The aqueous phase was acidified with 4N HCl and evaporated to dryness. The title compound was extracted with DCM/MeOH (9/1), pushed through a plug of Celite and was obtained after evaporation as a light yellow solid.

Workup

  1. customthe resulting reaction mixture
  2. extractionextracted with EtOAc
  3. customevaporated to dryness
  4. extractionThe title compound was extracted with DCM/MeOH (9/1)
  5. customwas obtained
  6. customafter evaporation as a light yellow solid

Sources & evidence

ORD record
ord-6ce0705c5ffd484099f75d861aa7dc4f
Source dataset
uspto-grants-2015_10
Patent number
US09163011B2

Reaction notes

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