Water → HCID 19898801, compound

HRID 1196487Notes

Reaction equation

HRID 1196487 reaction equation
C([O:3][C:4](=[O:21])[CH2:5][C:6]1[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:8][N:9]2[CH:14]=[CH:13][CH:12]=[N:11][C:10]=12)C.[OH-].[Na+].O>C(O)C>[C:15]1([C:7]2[C:6]([CH2:5][C:4]([OH:21])=[O:3])=[C:10]3[N:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 54499386HCID 54499386, compound

Product 1

HCID 19898801HCID 19898801, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 12.25 g (0.043 mole) of 2-phenylpyrazolo[1,5-a]pyrimidine-3-acetic acid ethyl ester in 100 ml of absolute ethanol was treated with 6.9 g (0.087 mole) of 50% sodium hydroxide and 35 ml of water and refluxed for 4 hours under a nitrogen atmosphere. The solvent was evaporated under reduced pressure and the residue was dissolved in water (100 ml). Acidification with glacial acetic acid produced a solid precipitate. The solid was collected by filtration to yield 10.8 g of crude product, mp 78°-90° C. Recrystallization from acetone-water, and then from toluene provided 8.25 g (75%) of product, mp 153°-156° C.

Workup

  1. temperaturerefluxed for 4 hours under a nitrogen atmosphere
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in water (100 ml)
  4. customAcidification with glacial acetic acid produced a solid precipitate
  5. filtrationThe solid was collected by filtration
  6. customto yield 10.8 g of crude product, mp 78°-90° C
  7. customRecrystallization from acetone-water

Sources & evidence

ORD record
ord-40b12d7dea654f16a10844e4d8b6d7be
Source dataset
uspto-grants-1992_05
Patent number
US05114944

Reaction notes

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