Lithium Hydroxide → HCID 22934095, compound

HRID 1269961Notes

Reaction equation

HRID 1269961 reaction equation
[OH-:1].[Li+].C([N:6]1[C:14]2[C:9](=[C:10]([CH3:20])[C:11](CC([O-])=O)=[CH:12][C:13]=2[CH3:15])[CH:8]=[N:7]1)(=O)C.[Cl-].[NH4+]>CO.O1CCCC1>[CH3:20][C:10]1[C:11]([OH:1])=[CH:12][C:13]([CH3:15])=[C:14]2[C:9]=1[CH:8]=[N:7][NH:6]2

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 25517Ammonium ChlorideHCID 18447072HCID 18447072, compound

Product 1

HCID 22934095HCID 22934095, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A 2N-aqueous lithium hydroxide solution (85 ml, 170 mmol) was added to a solution of (1-acetyl-4,7-dimethyl-1H-indazol-5-yl)acetate (20.3 g, 82.4 mmol) in methanol-tetrahydrofuran (1:1, 170 ml) under ice-cooling, and the resulting mixture was stirred at room temperature for 30 minutes. A saturated aqueous ammonium chloride solution was poured into the reaction solution, followed by extraction with ethyl acetate, and the extract solution was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate and then distilled under reduced pressure to remove the solvent. The residue was washed with acetonitrile by repulping to obtain 4,7-dimethyl-1H-indazol-5-ol (13.0 g, 97%).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washthe extract solution was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. washThe residue was washed with acetonitrile

Sources & evidence

ORD record
ord-59dad425e55f4175b54e354984ea49dc
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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