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

HRID 1755215Notes

Reaction equation

HRID 1755215 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([C:13]([O:15]CC)=[O:14])=[N:9]2)=[CH:4][CH:3]=1.[Li+].[OH-].Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[CH:11][C:10]([C:13]([OH:15])=[O:14])=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 14129378Ethyl 1-(4-chlorophenyl)pyrazole-3-carboxylate

Product 1

HCID 141293761-(4-chlorophenyl)-1H-pyrazole-3-carboxylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 1-(4-chlorophenyl)pyrazole-3-carboxylate (250 mg, 1 mmol) in THF was added 3.0 mL of 1.0 M of LiOH (3.0 mmol). The resulting mixture was stirred at room temperature for 3 h at which time 1.0 M HCl was added to adjust the pH to 1.0. The organics were extracted with EtOAc (2×100 mL), dried over MgSO4, and concentrated under reduced pressure to give a white solid (213 mg, 96%), which was used for next step without further purification.

Workup

  1. additionwas added
  2. extractionThe organics were extracted with EtOAc (2×100 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-445ff9c387794442bda07905c53d8fb9
Source dataset
uspto-grants-2015_10
Patent number
US09169261B2

Reaction notes

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