ChemicalBook CAS DataBase List 6-Hydroxyindazole

6-Hydroxyindazole synthesis

7synthesis methods

Product Name:6-Hydroxyindazole
CAS Number:23244-88-4
Molecular formula:C7H6N2O
Molecular Weight:134.14

6967-12-0 Synthesis

6967-12-0
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$9.00/1g

23244-88-4
167 suppliers
$28.00/1g

Yield:23244-88-4 87%

Reaction Conditions:

with sulfuric acid;water;sodium nitrite at 0 - 120;

Steps:

1 6.1.12. General procedure for the synthesis of 26 and 27
General procedure: To a suspension of corresponding amine (1 equiv) in H2O/98% H2SO4 (1:1) was added NaNO2 (1 equiv) slowly at 0 °C. After stirred at 120 °C for 2 h, the mixture was diluted with water (30 mL) and extracted with ethyl acetate (30 mL x 3). The combined organic layer was dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography (dichloromethane/methanol) to afford the desired products 26 and 27. 6.1.12.1
H-Indazol-6-ol (26)
Orange solid (yield: 87%).
¹H NMR (400 MHz, DMSO-d₆): δ 12.55 (s, 1H), 9.56 (s, 1H), 7.85 (s, 1H), 7.51 (d, J = 8.8 Hz, 1H), 6.75 (s, 1H), 6.62 (dd, J = 8.8, 1.6 Hz, 1H).

References:

Dong, Yan;Li, Kehuang;Xu, Zhixiang;Ma, Haikuo;Zheng, Jiyue;Hu, Zhilin;He, Sudan;Wu, Yiyuan;Sun, Zhijian;Luo, Lusong;Li, Jiajun;Zhang, Hongjian;Zhang, Xiaohu [Bioorganic and Medicinal Chemistry,2015,vol. 23,# 21,p. 6855 - 6868]

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