Hydrochloric Acid → 5-Chloro-3-fluoropyridine-2-carboxylic acid

HRID 1532562

Reaction equation

HRID 1532562 reaction equation
[F:1][C:2]1[C:3]([C:9]([O:11]CC)=[O:10])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[OH-].[Na+].Cl>CS(C)=O>[F:1][C:2]1[C:3]([C:9]([OH:11])=[O:10])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22013569Ethyl 5-chloro-3-fluoropicolinate

Product 1

HCID 117690705-Chloro-3-fluoropyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

70 g of ethyl 3-fluoro-5-chloro-2-pyridinecarboxylate (Example H1) are initially introduced into 105 ml of dimethyl sulfoxide (DMSO). 230 ml of a 2N sodium hydroxide solution are added dropwise at 40° C. in the course of 30 minutes. The resulting yellow suspension is introduced into a mixture of 2 l of ice-water and 400 ml of 2N hydrochloric acid. After subsequently stirring for 20 minutes, the mixture is filtered and the material on the filter is washed twice with water. 56.4 g of the desired target compound are obtained as a white solid.

Workup

  1. filtrationthe mixture is filtered
  2. washthe material on the filter is washed twice with water
  3. custom56.4 g of the desired target compound are obtained as a white solid

Sources & evidence

ORD record
ord-cb179efc163e446a9d32c52fa555818d
Source dataset
uspto-grants-2001_03
Patent number
US06204221B1

Linked notes

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