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

HRID 1612735Notes

Reaction equation

HRID 1612735 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+]>CO.O>[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

5

Reactant 2

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

Product 1

HCID 6891051H-Indazole-3-carboxylic acid, 1-methyl-Yield 92.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 1-methylindazole-3-carboxylic acid, methyl ester (1.00 g, 0.0053 mol) was stirred in a mixture of methanol (10 mL)/2 N NaOH solution (120 mL) at reflux temperature for 2 hours. After cooling, the mixture was diluted with water (100 mL) and acidified with 6 N HCI solution. The white solid that formed was collected by filtration and dried under ambient conditions for 6 days to give 0.86 g (92% yield) of the product; mp 215°-216° C.

Workup

  1. temperatureat reflux temperature for 2 hours
  2. temperatureAfter cooling
  3. customThe white solid that formed
  4. filtrationwas collected by filtration
  5. customdried under ambient conditions for 6 days

Sources & evidence

ORD record
ord-7ca6016db1b741a49705e280c4f76ddf
Source dataset
uspto-grants-1993_03
Patent number
US05190953

Reaction notes

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