Hydrochloric Acid → 2-(1-Benzyl-5-phenyl-1H-pyrazol-4-YL)acetic acid

HRID 349929Notes

Reaction equation

HRID 349929 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11](CC#N)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:22].[K+].Cl.[CH2:25]([OH:27])[CH3:26]>>[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]([CH2:26][C:25]([OH:22])=[O:27])[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 23024861(1-benzyl-5-phenyl-1H-pyrazol-4-yl)acetonitrile

Product 1

HCID 230247242-(1-Benzyl-5-phenyl-1H-pyrazol-4-YL)acetic acidYield 99%

Procedure

A mixture of (1-benzyl-5-phenyl-1H-pyrazol-4-yl)acetonitrile (3.50 g), a 4N aqueous potassium hydroxide solution (16 ml), and ethanol (50 ml) was refluxed for 4 hours. The reaction mixture was acidified with 1N hydrochloric acid, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated to obtain (1-benzyl-5-phenyl-1H-pyrazol-4-yl)acetic acid (3.70 g, yield: 99%) as a colorless oily substance.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a9d90f6648744fa5a87a01702b35a9bc
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

Loading…