Potassium Hydroxide → 4-Ethoxy-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

HRID 596762Notes

Reaction equation

HRID 596762 reaction equation
C([O:3][C:4]([C:6]1[C:7]([O:17][CH2:18][CH3:19])=[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-].[K+]>C(O)C>[CH2:18]([O:17][C:7]1[C:6]([C:4]([OH:5])=[O:3])=[CH:11][N:10]=[C:9]2[N:12]([CH2:15][CH3:16])[N:13]=[CH:14][C:8]=12)[CH3:19]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 13072976Ethyl 4-ethoxy-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

Product 1

HCID 130729804-Ethoxy-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

263 g. of 4-Ethoxy-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester (1 mol.) are heated with a solution of 114 g. of potassium hydroxide (2 mol.) in 1 liter of ethanol at 60° for 12 hours. After this time, the solvent is removed in vacuo and the residue is dissolved in 1.5 liters of water. After acidifying with acetic acid, 4-ethoxy-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid precipitates. Recrystallization from alcohol yields 215 g. (91%), m.p. 198°-199°.

Workup

  1. customAfter this time, the solvent is removed in vacuo
  2. dissolutionthe residue is dissolved in 1.5 liters of water
  3. customprecipitates
  4. customRecrystallization from alcohol
  5. customyields 215 g

Sources & evidence

ORD record
ord-bbc8240ca1744448892b43579cfd096b
Source dataset
uspto-grants-1977_03
Patent number
US04012373

Reaction notes

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