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

HRID 618664

Reaction equation

HRID 618664 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH3:14])[N:6]=1)=[O:4].[OH-].[Na+]>O1CCCC1>[CH3:14][N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]([C:3]([OH:4])=[O:2])=[N:6]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-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl-1-methylindazole-3-carboxylate (3.1 g, 0.016 mol) was stirred with a solution of sodium hydroxide (0.78 g, 0.02 mol) in tetrahydrofuran (100 ml) for 2 hours at room temperature, the solution evaporated and the yellow residue were dissolved in water. Acidification with methanesulfonic acid precipitated 1-methylindazole-3-carboxylic acid (2.19 g). A further crop (0.3 g) was obtained by extraction of the aqueous acid solution with a mixture of ether and methylene chloride. Total yield 2.49 g (87%).

Workup

  1. customthe solution evaporated
  2. dissolutionthe yellow residue were dissolved in water
  3. customAcidification with methanesulfonic acid precipitated 1-methylindazole-3-carboxylic acid (2.19 g)
  4. customA further crop (0.3 g) was obtained by extraction of the aqueous acid solution with a mixture of ether and methylene chloride

Sources & evidence

ORD record
ord-2aceac8fd9bc48ee985d35fc94fba092
Source dataset
uspto-grants-1999_09
Patent number
US05955470

Linked notes

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