Sodium Hydroxide → 2-Methyl-2H-indazole-3-carboxylic acid

HRID 1372741

Reaction equation

HRID 1372741 reaction equation
[CH3:1][N:2]1[C:10]([C:11]([O:13]C)=[O:12])=[C:9]2[C:4]([CH:5]=[CH:6][CH:7]=[CH:8]2)=[N:3]1.[OH-].[Na+]>C1COCC1>[CH3:1][N:2]1[C:10]([C:11]([OH:13])=[O:12])=[C:9]2[C:4]([CH:5]=[CH:6][CH:7]=[CH:8]2)=[N:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11658425Methyl 2-methyl-2H-indazole-3-carboxylate

Product 1

HCID 70605372-Methyl-2H-indazole-3-carboxylic acidYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To methyl 2-methylindazole-3-carboxylate (1.59 g, 8.36 mmol) were added THF (85 ml) and 0.25N NaOH (50 ml, 12.5 mmol) and the resulting mixture was stirred at room temperature for 24 hours. The reaction mixture was distilled under reduced pressure to remove the solvent. To the residue was added water, followed by the addition of 1N HCl (50 ml). The crystals thus precipitated were collected by filtration under reduced pressure, washed with water and dried under reduced pressure to give 2-methylindazole-3-carboxylic acid (1.34 g, 91%) as a colorless solid.

Workup

  1. distillationThe reaction mixture was distilled under reduced pressure
  2. customto remove the solvent
  3. additionTo the residue was added water
  4. additionfollowed by the addition of 1N HCl (50 ml)
  5. customThe crystals thus precipitated
  6. filtrationwere collected by filtration under reduced pressure
  7. washwashed with water
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-a49fee857c3c4b2b856781d27004a7ab
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Linked notes

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