Sodium Hydroxide → 1H-Indazole-5-carboxylic acid

HRID 626211Notes

Reaction equation

HRID 626211 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12]C)=[O:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[OH-].[Na+]>CO.O>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22260640Methyl 1H-indazole-5-carboxylate

Product 1

HCID 42484541H-Indazole-5-carboxylic acidYield 103.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of methyl 1H-indazole-5-carboxylate (6.5 g, 1.0 eq) in 200 mL MeOH was added a solution of NaOH (4.4 g, 3.0 eq) in 150 mL H2O. The mixture was refluxed for 1 h. The organic solvent was removed in vacuo, the remaining aqueous solution was washed with EtOAc, acidified with 3 N HCl to pH=5-6, and the precipitate was collected by filtration, and washed with water, to give the desired product as a yellow solid (6.2 g, 98%).

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. customThe organic solvent was removed in vacuo
  3. washthe remaining aqueous solution was washed with EtOAc
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-90627ddabdac46dfbe98960707ca596e
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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