Sodium Hydroxide → 5-(2,2,2-Trifluoroethoxy)pyridine-2-carboxylic acid

HRID 511842Notes

Reaction equation

HRID 511842 reaction equation
[F:1][C:2]([F:17])([F:16])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([O:13]CC)=[O:12])=[N:9][CH:10]=1.[OH-].[Na+]>CO>[F:17][C:2]([F:1])([F:16])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([OH:13])=[O:12])=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67291773Ethyl 5-(2,2,2-trifluoroethoxy)picolinate

Product 1

HCID 574758545-(2,2,2-Trifluoroethoxy)pyridine-2-carboxylic acidYield 53.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 5-(2,2,2-trifluoroethoxy)picolinate (253 mg, 1.0 mmol) and 2 mol/L aqueous sodium hydroxide solution (1.0 mL, 2.0 mmol) in methanol (5 mL) was stirred at room temperature for 4 h. Then, methanol was removed in vacuo. To the residue were added water (2 mL) and 2 mol/L hydrochloric acid (pH˜4). The formed precipitate was collected by filtration to give 118 mg (52% yield) of the title compound as a gray solid:

Workup

  1. customThen, methanol was removed in vacuo
  2. additionTo the residue were added water (2 mL) and 2 mol/L hydrochloric acid (pH˜4)
  3. filtrationThe formed precipitate was collected by filtration

Sources & evidence

ORD record
ord-7118358fcc5d4b8db297da7164d6e77f
Source dataset
uspto-grants-2015_08
Patent number
US09101616B2

Reaction notes

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