Lithium Hydroxide → 7-Methyl-1H-indazol-5-ol

HRID 1269960Notes

Reaction equation

HRID 1269960 reaction equation
[OH-:1].[Li+].C([N:6]1[C:14]2[C:9](=[CH:10][C:11](CC([O-])=O)=[CH:12][C:13]=2[CH3:15])[CH:8]=[N:7]1)(=O)C.[Cl-].[NH4+]>CO.O1CCCC1>[CH3:15][C:13]1[CH:12]=[C:11]([OH:1])[CH:10]=[C:9]2[C:14]=1[NH:6][N:7]=[CH:8]2

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 25517Ammonium ChlorideHCID 18447074HCID 18447074, compound

Product 1

HCID 229334627-Methyl-1H-indazol-5-olYield 93.1%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A 2N-aqueous lithium hydroxide solution (3.7 ml, 7.4 mmol) was added to a solution of (1-acetyl-7-methyl-1H-indazol-5-yl)acetate (850 mg, 3.66 mmol) in methanol-tetrahydrofuran (1:1, 7.4 ml), 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 purified by a silica gel column chromatography (eluent: chloroform/methanol=100:3) to obtain 7-methyl-1H-indazol-5-ol (505 mg, 93%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washthe extract solution was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=100:3)

Sources & evidence

ORD record
ord-02b0a9accffd46ecbe817a002f12a419
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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