Hydrochloric Acid → 1-(3-fluorophenyl)-1H-pyrazole-3-carboxylic acid

HRID 1755217Notes

Reaction equation

HRID 1755217 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[CH:11][C:10]([C:13]([O:15]CC)=[O:14])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[Li+].[OH-].Cl>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[CH:11][C:10]([C:13]([OH:15])=[O:14])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 47078632HCID 47078632, compound

Product 1

HCID 431238541-(3-fluorophenyl)-1H-pyrazole-3-carboxylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 1-(3-fluorophenyl)pyrazole-3-carboxylate (234 mg, 1 mmol) in THF was added 3.0 mL of 1.0M of LiOH (3.0 mmol). The resulting mixture was stirred at room temperature for 3 h and then 1.0 M of HCl was added to adjust pH to 1.0. The organics were extracted with EtOAc (2×100 mL), followed by drying over MgSO4 and concentrated under reduced pressure to give a white solid (198 mg, 96%), which was used for next step without further purification.

Workup

  1. extractionThe organics were extracted with EtOAc (2×100 mL)
  2. dry with materialby drying over MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-be9e5e94841c44b2bd8d16452800fce6
Source dataset
uspto-grants-2015_10
Patent number
US09169261B2

Reaction notes

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