Ethanol → 1-Ethyl-1H-pyrazolo[3,4-b]pyridine-4,5-dicarboxylic acid

HRID 429045Notes

Reaction equation

HRID 429045 reaction equation
C(C1[C:8]([C:9]([O:11]CC)=[O:10])=[CH:7][N:6]=[C:5]2[N:14]([CH2:17][CH3:18])[N:15]=[CH:16][C:4]=12)#N.[OH-:19].[Na+].[CH2:21]([OH:23])[CH3:22]>O>[CH2:17]([N:14]1[C:5]2=[N:6][CH:7]=[C:8]([C:9]([OH:11])=[O:10])[C:22]([C:21]([OH:19])=[O:23])=[C:4]2[CH:16]=[N:15]1)[CH3:18]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 867575834-Cyano-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid, ethyl ester

Product 1

HCID 183543231-Ethyl-1H-pyrazolo[3,4-b]pyridine-4,5-dicarboxylic acidYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Cyano-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid, ethyl ester (2.0 g, 8.2 mmol) was suspended in ethanol (20 mL), and an aqueous solution of NaOH (6 N, 3 eq) was added. The reaction mixture was heated at reflux for 2 h and then diluted with water (100 mL). This aqueous solution was extracted with diethyl ether (50 mL×2) and the organic extracts were discarded. The aqueous layer was then acidified with phosphoric acid and extracted with EtOAc (50 mL×3). The extracts were concentrated via evaporation under reduced pressure to afford the title compound (>90% purity, 50-90% yield). This material was used directly without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. extractionThis aqueous solution was extracted with diethyl ether (50 mL×2)
  4. extractionextracted with EtOAc (50 mL×3)
  5. concentrationThe extracts were concentrated via evaporation under reduced pressure

Sources & evidence

ORD record
ord-1145d9fad09f4256a70f1d7f841bd58f
Source dataset
uspto-grants-2001_11
Patent number
US06316438B1

Reaction notes

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