Hydrochloric Acid → 1-Phenyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid

HRID 2236188Notes

Reaction equation

HRID 2236188 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:17]([F:20])([F:19])[F:18])=[N:8][N:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:10]=1)=[O:5])C.[OH-].[Na+].Cl>CO>[C:11]1([N:9]2[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[C:7]([C:17]([F:19])([F:20])[F:18])=[N:8]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11448972Ethyl 1-phenyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 149682451-Phenyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (160 mg, 0.56 mmol) and 1N aqueous sodium hydroxide solution (2.3 mL, 2.3 mmol) in methanol (10 mL) was stirred at room temperature overnight. The reaction mixture was acidified to pH˜2 with 1N aqueous hydrochloric acid and concentrated to give 1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid as an off-white solid, which was directly used without further purification. LCMS calcd for C11H7F3N2O (m/e) 256, obsd 257 (M+H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-dd344b0fe57240b5b6b5afc906217c3a
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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