Acetic Acid → HCID 178463029, compound

HRID 1658749Notes

Reaction equation

HRID 1658749 reaction equation
C([O:3][C:4]([C:6]1[C:7]([OH:17])=[C:8]2[CH:14]=[N:13][N:12]([CH2:15][CH3:16])[C:9]2=[N:10][CH:11]=1)=[O:5])C.[OH-].[Na+].C(O)(=O)C>O>[CH2:15]([N:12]1[C:9]2=[N:10][CH:11]=[C:6]([C:4]([OH:5])=[O:3])[C:7]([OH:17])=[C:8]2[CH:14]=[N:13]1)[CH3:16]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 178469631HCID 178469631, compound

Product 1

HCID 178463029HCID 178463029, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

47 g of 1-ethyl-4-hydroxy-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester (0.2 mol) are saponified by means of 400 ml of aqueous sodium hydroxide (2.5 N) by refluxing the mixture for 1 1/2 hours. After cooling of the filtering solution and diluting with 300 ml of water, it is acidified with glacial acetic acid. The precipitated 1-ehyl-4-hydroxy-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid is filtered under suction, washed with water and dried at 120°. Yield 37 g (89%), recrystallization from glacial acetic acid, and has a melting point of 201°-292°.

Workup

  1. temperatureby refluxing the mixture for 1 1/2 hours
  2. temperatureAfter cooling of the filtering solution
  3. filtrationThe precipitated 1-ehyl-4-hydroxy-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid is filtered under suction
  4. washwashed with water
  5. customdried at 120°
  6. customYield 37 g (89%), recrystallization from glacial acetic acid

Sources & evidence

ORD record
ord-5410aa78352a4a44aec6ab8c48e34a05
Source dataset
uspto-grants-1976_06
Patent number
US03966746

Reaction notes

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