Water → 1-Benzyl-1H-pyrazole-4-carboxylic acid

HRID 928403Notes

Reaction equation

HRID 928403 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]([O:15]CC)=[O:14])[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O[Li].O>CO>[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 15237993ethyl 1-benzyl-1H-pyrazole-4-carboxylate

Product 1

HCID 64838761-Benzyl-1H-pyrazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 1-benzyl-1H-pyrazole-4-carboxylate (1.05 g, 3.56 mmol) was dissolved in MeOH (20 ml). Water (10 ml) and LiOH.H2O (0.299 g, 7.11 mmol) were added and the suspension was stirred for 3 h at rt. The reaction mixture was evaporated in vacuum to remove the MeOH. The water phase was washed with AcOEt, then treated with 1N HCl until pH3, and extracted with AcOEt. The organic phase was dried over MgSO4 and evaporated in vacuum to give the title compound which was used in the next step without any further purification. HPLC/MS (Method A) RtA=1.3 min, MS [M+H]+=203.1.

Workup

  1. customThe reaction mixture was evaporated in vacuum
  2. customto remove the MeOH
  3. washThe water phase was washed with AcOEt
  4. additiontreated with 1N HCl until pH3
  5. extractionextracted with AcOEt
  6. dry with materialThe organic phase was dried over MgSO4
  7. customevaporated in vacuum

Sources & evidence

ORD record
ord-3b3232f04cd643478ce4dc8d5a02511d
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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