Water → 6-methyl-1H-indazol-5-ol

HRID 1269823Notes

Reaction equation

HRID 1269823 reaction equation
[OH-].[Li+].C([O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[CH3:16])[N:12](C(=O)C)[N:11]=[CH:10]2)(=O)C.S([O-])(O)(=O)=O.[K+].O>CO.O1CCCC1>[CH3:16][C:15]1[CH:14]=[C:13]2[C:9]([CH:10]=[N:11][NH:12]2)=[CH:8][C:7]=1[OH:6]

Participants

7

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 516920Potassium bisulfateHCID 694307581-acetyl-6-methyl-1H-indazol-5-yl acetate

Product 1

HCID 229340186-methyl-1H-indazol-5-olYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 2M-aqueous lithium hydroxide solution (1.46 ml, 2.93 mmol) was added dropwise to a solution of 1-acetyl-6-methyl-1H-indazol-5-yl acetate (340 mg, 1.46 mmol) in a mixture of methanol (2.0 ml) and tetrahydrofuran (1.0 ml) at room temperature. After 1 hour, the reaction mixture was adjusted to pH 4 with a 0.5M-aqueous potassium hydrogensulfate solution. The resulting solution was poured into water (50 ml) and extracted with ethyl acetate (30 ml×3), and the extract solution was dried over anhydrous magnesium sulfate. The extract solution dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 6-methyl-1H-indazol-5-ol (199 mg, 92%).

Workup

  1. extractionextracted with ethyl acetate (30 ml×3)
  2. dry with materialthe extract solution was dried over anhydrous magnesium sulfate
  3. customThe extract solution dried
  4. concentrationwas concentrated under reduced pressure
  5. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3700daeff9204b4b9156fef467cf8cb0
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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