Water → 7-chloro-1H-indazole-5-carboxylic acid
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]2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- temperatureThe reaction mixture was heated
- temperatureat reflux for 16 hours
- extractionextracted twice with ethyl ether
- 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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