Hydrochloric Acid → 5-(Difluoromethoxy)picolinic acid

HRID 1693201Notes

Reaction equation

HRID 1693201 reaction equation
[OH-].[Na+].[F:3][CH:4]([F:16])[O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([O:14]C)=[O:13])=[N:10][CH:11]=1.Cl.[Cl-].[Na+]>CO.C(OCC)(=O)C>[F:16][CH:4]([F:3])[O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([OH:14])=[O:13])=[N:10][CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 57827732Methyl 5-(difluoromethoxy)picolinate

Product 1

HCID 574758715-(Difluoromethoxy)picolinic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 2 N sodium hydroxide solution (3.74 mL) was added to a solution of methyl 5-difluoromethoxypyridine-2-carboxylate obtained in Preparation Example 49-(1) (760 mg) in methanol (15 mL), and the mixture was stirred at room temperature for 30 minutes. The reaction solution was made acidic with hydrochloric acid. Saturated aqueous sodium chloride and ethyl acetate were added to the reaction solution, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain the title compound (482 mg).

Workup

  1. customthe organic layer was separated
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ae6b13f4e61f44c596f90957c8292411
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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