Hydrochloric Acid → 1-methyl-4,5,6,7-tetrahydro-1H-indazole-4-carboxylic acid

HRID 62443Notes

Reaction equation

HRID 62443 reaction equation
[CH3:1][N:2]1[C:10]2[CH2:9][CH2:8][CH2:7][CH:6]([C:11]([O-:13])=[O:12])[C:5]=2[CH:4]=[N:3]1.[Li+].[OH-].Cl>CO.C1COCC1.O>[CH3:1][N:2]1[C:10]2[CH2:9][CH2:8][CH2:7][CH:6]([C:11]([OH:13])=[O:12])[C:5]=2[CH:4]=[N:3]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 1317371911-methyl-4,5,6,7-tetrahydro-1H-indazole-4-carboxylate

Product 1

HCID 772303371-methyl-4,5,6,7-tetrahydro-1H-indazole-4-carboxylic acidYield 94%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-methyl-4,5,6,7-tetrahydro-1H-indazole-4-carboxylate (7 g, 36 mmol) in methanol (100 mL), THF (50 mL) and H2O (50 mL) was added LiOH (2.5 g, 108 mmol). The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was acidified with 1N HCl solution to pH=5-6, and extracted with EA three times. The combined organic layers were washed with brine, dried over Na2SO4. The solvent was concentrated to give 1-methyl-4,5,6,7-tetrahydro-1H-indazole-4-carboxylic acid (6 g, 94%), which was used in the next step directly.

Workup

  1. extractionextracted with EA three times
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-fd084183767c4a3fbb410b56931aa556
Source dataset
uspto-grants-2016_09
Patent number
US09446130B2

Reaction notes

Loading…