Hydrochloric Acid → 4-(4-phenyl-1H-pyrazol-1-yl)butanoic acid

HRID 1787822Notes

Reaction equation

HRID 1787822 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][N:10]([CH2:12][CH2:13][CH2:14][C:15]([O:17]CC)=[O:16])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>CO.[OH-].[Na+]>[C:1]1([C:7]2[CH:8]=[N:9][N:10]([CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66725907ethyl 4-(4-phenyl-1H-pyrazol-1-yl)butanoate

Product 1

HCID 576002864-(4-phenyl-1H-pyrazol-1-yl)butanoic acidYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of ethyl 4-(4-phenyl-1H-pyrazol-1-yl)butanoate (273 mg, 1.06 mmole) in methanol (5 ml) and 1N NaOH (5 mL) was stirred at room temperature for 2 hours. The reaction mixture was adjusted to be acidic (pH=3-4) with 6 N HCl with an ice bath and then extracted with EtOAc (3×). The combined organic phases were washed with water and brine, dried over Na2SO4, filtered and concentrated to give the desired product (190 mg, 78%). LCMS calculated for C13H15N2O2 (M+H): 231.1; found: 231.1.

Workup

  1. extractionextracted with EtOAc (3×)
  2. washThe combined organic phases were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8caad14f2992442898e4732fb72846ce
Source dataset
uspto-grants-2009_03
Patent number
US07511050B2

Reaction notes

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