Hydrochloric Acid → 1-(4-Fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid

HRID 559624Notes

Reaction equation

HRID 559624 reaction equation
C([O:3][C:4]([C:6]1[C:7]2[CH:14]=[N:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:8]=2[CH:9]=[N:10][CH:11]=1)=[O:5])C.[OH-].[K+].Cl>CO.O.O>[F:21][C:18]1[CH:19]=[CH:20][C:15]([N:12]2[C:8]3[CH:9]=[N:10][CH:11]=[C:6]([C:4]([OH:5])=[O:3])[C:7]=3[CH:14]=[N:13]2)=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 592784101-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid ethyl ester

Product 1

HCID 592781371-(4-Fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid ethyl ester (2.75 g, 9.64 mmol) and 85% potassium hydroxide pellets (6.4 g, 84 mmol) in methanol-water was warmed at reflux for 15 minutes and then stirred overnight. The mixture was then diluted with water (300 mL) and then a dilute solution of aqueous HCl (1 equivalent based on mass of KOH) was added in several portions (final pH=5). The resulting solid was collected by filtration and dried by pulling vacuum through the filter cake to afford 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid.

Workup

  1. temperaturewas warmed
  2. temperatureat reflux for 15 minutes
  3. filtrationThe resulting solid was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-b7eecd99505741c5b2ec6ed24ba9dec5
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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