Sodium Hydroxide → 1-(2-Pyridinyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid

HRID 1941883Notes

Reaction equation

HRID 1941883 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16]([O:18]CC)=[O:17])[CH:9]=[N:8]1.[OH-].[Na+]>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:11]([C:12]([F:14])([F:15])[F:13])=[C:10]([C:16]([OH:18])=[O:17])[CH:9]=[N:8]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58504358ethyl 1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 167877231-(2-Pyridinyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acidYield 71.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate (8.7 g, 30.5 mmol) in ethanol (2 mL) was added 3 N NaOH (30.5 mL, 92 mmol). After the reaction was stirred at room temperature for 1 hour, the solvents were evaporated and 3N aq. HCl was added. The resulting solids were collected by filtration to afford 1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (5.58 g, 21.7 mmol). The compound had an HPLC retention time=2.0 min. —Column: PHENOMENEX® Luna 5u C18 4.6×30 mm (2 min.); Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA. LC/MS M+1=258.1.

Workup

  1. customthe solvents were evaporated
  2. addition3N aq. HCl was added
  3. filtrationThe resulting solids were collected by filtration

Sources & evidence

ORD record
ord-393738f29eeb4694a674e63a4cd3df37
Source dataset
uspto-grants-2013_03
Patent number
US08389509B2

Reaction notes

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