Hydrochloric Acid → [2-Methyl-5-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-acetic acid

HRID 915419Notes

Reaction equation

[CH3:1][N:2]1[C:6]([CH2:7][C:8]#N)=[CH:5][C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[N:3]1.[OH-:20].[Na+].[OH2:22].Cl>C(O)C>[CH3:1][N:2]1[C:6]([CH2:7][C:8]([OH:22])=[O:20])=[CH:5][C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[N:3]1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of [2-methyl-5-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-acetonitrile (267 mg, 1 mmol), sodium hydroxide (403 mg, 10 mmol), water (4 ml) and ethanol (4 ml) was stirred vigorously at 85° C. for 14 h. The reaction mixture was poured onto crushed ice and aqueous HCl and extracted three times with ethyl acetate. The combined extracts were washed with water and brine, and dried over anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure gave 286 mg (1 mmol, quant.) of the title compound as off-white crystals.

Workup

additionThe reaction mixture was poured
extractionextracted three times with ethyl acetate
washThe combined extracts were washed with water and brine
dry with materialdried over anhydrous sodium sulfate
customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record: ord-d4521e7eeee24741947b0ff19dddd062
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265149B2

Reaction notes

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