Sodium Hydroxide → 1H-Indazole-3-carboxylic acid, 1-methyl-

HRID 1372739Notes

Reaction equation

HRID 1372739 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([O:13]C)=[O:12])=[N:3]1.[OH-].[Na+]>C1COCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([OH:13])=[O:12])=[N:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13900574Methyl 1-methyl-1H-indazole-3-carboxylate

Product 1

HCID 6891051H-Indazole-3-carboxylic acid, 1-methyl-Yield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF (250 ml) was dissolved methyl 1-methylindazole-3-carboxylate (4.49 g, 23.6 mmol). To the resulting solution was added 0.25N NaOH (145 ml, 35.4 mmol), followed by stirring at room temperature for 24 hours. The reaction mixture was distilled under reduced pressure to remove the solvent. To the residue was added 1N HCl (145 ml). The crystals thus precipitated were collected by filtration under reduced pressure, washed with water, and dried under reduced pressure to give 1-methylindazole-3-carboxylic acid (2.81 g, 68%) as a pale yellow solid.

Workup

  1. distillationThe reaction mixture was distilled under reduced pressure
  2. customto remove the solvent
  3. additionTo the residue was added 1N HCl (145 ml)
  4. customThe crystals thus precipitated
  5. filtrationwere collected by filtration under reduced pressure
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-1fe73d0317884d718f26e0c4b50c1627
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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