Potassium Hydroxide → 1-(4-Methoxyphenyl)-1H-pyrazole

HRID 2186238Notes

Reaction equation

HRID 2186238 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[CH:12][C:11](C(OCC)=O)=[N:10]2)=[CH:5][CH:4]=1.[OH-].[K+]>C1COCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH:13]=[CH:12][CH:11]=[N:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 143726701-[(4-methoxy)phenyl]-3-(ethoxycarbonyl)-1H-pyrazole

Product 1

HCID 122381311-(4-Methoxyphenyl)-1H-pyrazoleYield 142.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution 1-[(4-methoxy)phenyl]-3-(ethoxycarbonyl)-1H-pyrazole-5-[(4-(N-pyrrolidinocarbonyl)phenyl)carboxyamide (2.05 g, 4.43 mmol) in 10 mL of THF and 10 mL of water was added potassium hydroxide (0.32 g, 5.76 mmol). The resulting solution was stirred at ambient temperature for 18. The THF was removed in vacuo and the aqueous was extracted with ether to remove unreacted ester. The aqueous layer was acidified with HCl and extracted with ethyl acetate. The organics were washed with brine, dried (MgSO4) and concentrated to afford 1.1 g (57%) of the title compound, which was used without further purification. LRMS (ES−): 433.0 (M−H)−.

Workup

  1. customThe THF was removed in vacuo
  2. extractionthe aqueous was extracted with ether
  3. customto remove unreacted ester
  4. extractionextracted with ethyl acetate
  5. washThe organics were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-55faa003ce4646439e342f29ecff4919
Source dataset
uspto-grants-2002_06
Patent number
US06403620B1

Reaction notes

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