Sodium Hydroxide → 6-Methoxy-1H-indazole-3-carboxylic acid

HRID 245753Notes

Reaction equation

HRID 245753 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:12]([O:14]CC)=[O:13])=[N:8][NH:9]2)=[CH:5][CH:4]=1.[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:12]([OH:14])=[O:13])=[N:8][NH:9]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 45141401Ethyl 6-methoxy-1H-indazole-3-carboxylate

Product 1

HCID 224776586-Methoxy-1H-indazole-3-carboxylic acidYield 80.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To ethyl 6-methoxy-1H-indazole-3-carboxylate (0.415 mmol) in methanol (5 ml) was added 4N sodium hydroxide (aq) (8 mL, 32.0 mmol). After two hours stirring, reaction was still not finished and 6 ml of 4N NaOH was added. Upon completion of the reaction, the methanol was removed by evaporation and the water layer was washed with ethyl acetate. Subsequently the water layer was acidified and extracted with ethyl acetate twice. The latter organic layers were combined, dried (Na2SO4) and concentrated in vacuo to give 6-methoxy-1H-indazole-3-carboxylic acid (64 mg) as a brown solid.

Workup

  1. customreaction
  2. customUpon completion of the reaction
  3. customthe methanol was removed by evaporation
  4. washthe water layer was washed with ethyl acetate
  5. extractionextracted with ethyl acetate twice
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-206c20e415b14e938b468fe4e4330633
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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