Water → HCID 19898809, compound

HRID 345506Notes

Reaction equation

HRID 345506 reaction equation
Cl.C([O:4][C:5](=[O:19])[CH2:6][C:7]1[C:8]([NH2:18])=[N:9][NH:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)C.[OH-].[Na+].O>CCO>[NH2:18][C:8]1[C:7]([CH2:6][C:5]([OH:19])=[O:4])=[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:10][N:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67913303HCID 67913303, compound

Product 1

HCID 19898809HCID 19898809, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4.1 g (0.014 mole) of 3-amino-5-phenyl-1H-pyrazole-4-acetic acid ethyl ester (Example I free base) in 50 ml of absolute EtOH was treated with 1.23 g (0.016 mole) of 50% NaOH and 10 ml of water, and the mixture was refluxed for 4 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure and the residue was dissolved in water (10 ml). The pH was adjusted to approximately 6.5 with glacial acetic acid, and a solid precipitated. The solid was collected by filtration to give 1.6 g of product, mp 214°-216° C. with effervesence (50% yield).

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in water (10 ml)
  4. customa solid precipitated
  5. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-92a53e4834174a57a303074bb2015e6d
Source dataset
uspto-grants-1991_10
Patent number
US05057534

Reaction notes

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