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

HRID 923308Notes

Reaction equation

HRID 923308 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 93.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 1H-indazole-5-carboxylate (10 g, 56.82 mmol) in methanol (80 ml) was added a solution of sodium hydroxide (9.09 g, 227.28 mmol) in water (30 ml) with stirring overnight at 60° C. in an oil bath. The resulting mixture was concentrated under vacuum, then quenched by the addition of water (30 ml), and the pH adjusted to 6 with HCl (3N). The solids were collected by filtration to afford 1H-indazole-5-carboxylic acid as a yellow solid (8.6 g, 93%). LC/MS (ES, m/z): [M+H]+ 163.0

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. customquenched by the addition of water (30 ml)
  3. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-82618bfe307c446ba3d4ace534858937
Source dataset
uspto-grants-2016_03
Patent number
US09278973B2

Reaction notes

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