ChemicalBook CAS DataBase List 1H-Indazol-5-ol

1H-Indazol-5-ol synthesis

7synthesis methods

Product Name:1H-Indazol-5-ol
CAS Number:15579-15-4
Molecular formula:C7H6N2O
Molecular Weight:134.14

94444-96-9 Synthesis

94444-96-9
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$24.00/250mg

15579-15-4
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$5.00/250mg

Yield: 71%

Reaction Conditions:

with boron tribromide in dichloromethane at 20; for 10 h;

Steps:

4.b Reference Example 4; Synthesis of 1H-indazol-5-ol; (b) Synthesis of 1H-indazol-5-ol
A methylene chloride solution of boron tribromide (18.5 ml, 18.5 mmol) was added to a solution of 5-methoxy-1H-indazole (1.24 g, 8.40 mmol) in methylene chloride (84 ml) at 0°C and stirred at room temperature for 10 hours. Then, water was poured into the reaction solution in an ice-water bath, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to remove the solvent, and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol = 96/4) to obtain 1H-indazol-5-ol (877 mg, 71%).1H-NMR (DMSO-d6) δ; 6.88 (1H, dd, J=8.8, 2.2Hz), 6.96 (1H, d, J=2.2Hz), 7.34 (1H, d, J=8.8Hz), 7.84 (1H, s).

References:

Sumitomo Pharmaceuticals Company, Limited EP1403255, 2004, A1 Location in patent:Page 44