Acetic Acid → HCID 19898798, compound

HRID 1196486Notes

Reaction equation

HRID 1196486 reaction equation
C([O:3][C:4](=[O:22])[CH2:5][C:6]1[C:7]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[N:8][N:9]2[CH:14]=[CH:13][CH:12]=[N:11][C:10]=12)C.[OH-].[Na+].C(O)C.C(O)(=O)C>O>[CH3:21][C:18]1[CH:17]=[CH:16][C:15]([C:7]2[C:6]([CH2:5][C:4]([OH:22])=[O:3])=[C:10]3[N:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 54485817HCID 54485817, compound

Product 1

HCID 19898798HCID 19898798, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A stirred mixture of 32.5 g (0.11 mole) of 2-(4-methylphenyl)pyrazolo[1,5-a]pyrimidine-3-acetic acid ethyl ester and 4.5 g (0.11 mole) of sodium hydroxide in 150 mL of 190 ethanol was heated until the material dissolved. After cooling, the reaction mixture was diluted with an equal volume of water, heated until a clear dark brown solution was obtained, then cooled by stirring overnight. The reaction mixture was diluted with an additional 300 mL of water and acidified to pH 6 with glacial acetic acid. The milky solution yielded 27 g (90%) of brown crystalline product, mp 170°-171°. An analytical sample recrystallized from acetonitrile-water yielding pale yellow crystals, mp. 172°-173° C.

Workup

  1. temperaturewas heated until the material
  2. dissolutiondissolved
  3. temperatureAfter cooling
  4. temperatureheated until a clear dark brown solution
  5. customwas obtained
  6. temperaturecooled

Sources & evidence

ORD record
ord-da99a60f47ee4b8d8314d513af8d0dc5
Source dataset
uspto-grants-1992_05
Patent number
US05114944

Reaction notes

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