ChemicalBook CAS DataBase List 5-METHOXY-1H-INDAZOLE

5-METHOXY-1H-INDAZOLE synthesis

6synthesis methods

Product Name:5-METHOXY-1H-INDAZOLE
CAS Number:94444-96-9
Molecular formula:C8H8N2O
Molecular Weight:148.16

102-50-1 Synthesis

102-50-1
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94444-96-9
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Yield: 18%

Reaction Conditions:

with acetic acid;sodium nitrite in water at 20;

Steps:

4.a Reference Example 4; Synthesis of 1H-indazol-5-ol; (a) Synthesis of 5-methoxy-1H-indazole
A solution of sodium nitrite (3.38 g, 49.0 mmol) in water (8.1 ml) was added to a solution of 4-methoxy-2-methylaniline (6.69 g, 48.8 mmol) in acetic acid (350 ml) in an ice-water bath while maintaining the temperature at 25°C or lower, and stirred overnight at room temperature. Then, the reaction solution was poured into water and extracted with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and then distilled under reduced pressure to remove the solvent, and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol = 9/1) to obtain 5-methoxy-1H-indazole (1.30 g, 18%).1H-NMR (DMSO-d6) δ; 3.76 (3H, s), 6.98 (1H, dd, J=8.8, 1.8Hz), 7.15 (1H, d, J=1.8Hz), 7.42 (1H, d, J=8.8Hz), 7.93 (1H, s), 12.89 (1H, brs).

References:

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