Water → Indazole-3-carboxylic acid

HRID 1372736Notes

Reaction equation

HRID 1372736 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([O:15]C)=[O:14])=[N:5]1)(=O)C.[OH-].[Na+].O>Cl>[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([OH:15])=[O:14])=[N:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 3681967Methyl 1-acetylindazole-3-carboxylate

Product 1

HCID 78250Indazole-3-carboxylic acidYield 108.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
65 °C

Procedure

To methyl 1-acetylindazole-3-carboxylate (22.3 g, 0.10 mol) were added sodium hydroxide (8.18 g, 0.20 mol) and water (640 ml) and the resulting mixture was stirred at 60 to 70° C. for 6.5 hours. The reaction mixture was poured in concentrated HCl (30 ml). The crystals thus precipitated were collected by filtration under reduced pressure, washed with water and dried under reduced pressure to give indazole-3-carboxylic acid (17.6 g, 100%) as a pale yellow solid.

Workup

  1. customThe crystals thus precipitated
  2. filtrationwere collected by filtration under reduced pressure
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-0360e4640d5a40cf84a61038dc4d5b79
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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