Lithium Hydroxide → 3-(2,2,2-Trifluoroethoxy)pyridine-2-carboxylic acid

HRID 517072Notes

Reaction equation

HRID 517072 reaction equation
C[O:2][C:3]([C:5]1[C:10]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=[CH:7][N:6]=1)=[O:4].[OH-].[Li+]>CO.O>[F:16][C:13]([F:14])([F:15])[CH2:12][O:11][C:10]1[C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 574758803-(2,2,2-Trifluoro-ethoxy)-pyridine-2-carboxylic acid methyl ester

Product 1

HCID 574758793-(2,2,2-Trifluoroethoxy)pyridine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 3-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid methyl ester (216 mg, 0.9 mmol) in methanol (1 ml) was treated with a solution of lithium hydroxide (78 mg, 3.3 mmol) in water (0.1 ml) and stirring was continued at 22° C. for 2 hours. The solution was evaporated and the residue triturated with 1N aqueous hydrochloric acid. The suspension was filtered, the residue washed with water and dried to give 3-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid as a colorless solid. MS (ISN): m/z=220 [M−H]−.

Workup

  1. customThe solution was evaporated
  2. customthe residue triturated with 1N aqueous hydrochloric acid
  3. filtrationThe suspension was filtered
  4. washthe residue washed with water
  5. customdried

Sources & evidence

ORD record
ord-db7e7c34baea41cbb7c0f56e6ca1b703
Source dataset
uspto-grants-2015_08
Patent number
US09115098B2

Reaction notes

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