Hydrochloric Acid → Pyrazole-5-carboxylic acid, 3-phenyl-

HRID 2369836Notes

Reaction equation

HRID 2369836 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([C:12]([O:14]C)=[O:13])[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[OH-].Cl>C1COCC1.O>[C:1]1([C:7]2[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[NH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 644585methyl 3-phenyl-1H-pyrazole-5-carboxylate

Product 1

HCID 121025Pyrazole-5-carboxylic acid, 3-phenyl-Yield 57.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-phenyl-1H-pyrazole-5-carboxylate (6.02 g, 29.8 mmol) in THF and H2O (3:1, 140 mL) was added LiOH (3.42 g, 142.8 mmol) and the mixture was stirred overnight at room temperature. It was poured into 2N HCl solution (150 mL) and extracted with ethyl acetate. After extration, the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated at reduced pressure to afford product (3.2 g, 57.1%): MS (EI) for C10H8N2O2: 189.26 (MH+).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialAfter extration, the organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-833b35e2f6e74ff492cf0e0deb503280
Source dataset
uspto-grants-2014_04
Patent number
US08710038B2

Reaction notes

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