Water → 1031417-54-5

HRID 1892576Notes

Reaction equation

HRID 1892576 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]#N)[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2.[OH2:13].[OH-:14].[K+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:11]([OH:14])=[O:13])[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 669205317-Chloro-1H-indazole-5-carbonitrile

Product 1

HCID 582525981031417-54-5Yield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 7-chloro-1H-indazole-5-carbonitrile (1.36 g, 7.66 mmol) in ethanol (52.5 mL) was added water (17.5 mL) and potassium hydroxide (6.44 g, 115 mmol). The reaction mixture was heated at reflux for 16 hours. The reaction mixture was cooled to room temperature, extracted twice with ethyl ether, acidified the aqueous with 1N hydrochloric acid and the resultant precipitate was filtered to afford 7-chloro-1H-indazole-5-carboxylic acid as a brown solid (900 mg, 60%): −ESI MS (M−H) 195.2.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 hours
  3. extractionextracted twice with ethyl ether
  4. filtrationthe resultant precipitate was filtered

Sources & evidence

ORD record
ord-51670a19323740ae9abf67f253d3f8b1
Source dataset
uspto-grants-2013_08
Patent number
US08507681B2

Reaction notes

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