ChemicalBook CAS DataBase List 5,7-Diiodo-8-quinolinol

5,7-Diiodo-8-quinolinol synthesis

5synthesis methods

Product Name:5,7-Diiodo-8-quinolinol
CAS Number:83-73-8
Molecular formula:C9H5I2NO
Molecular Weight:396.95

Iodoquinol, 5,7-diiodo-8-quinolinol (37.2.2), is made by iodination of 8-oxyquinoline (37.2.1) using a mixture of potassium iodide/potassium iodate. The initial 8-hydroxyquinolin (37.2.1) is made from 2-aminophenol and glycerol in the presence of sulfuric acid and nitrobenzene (Skraup synthesis).

148-24-3 Synthesis

148-24-3
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83-73-8
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$6.00/250mg

Yield:83-73-8 87%

Reaction Conditions:

with 1-butyl-3-methyl-pyridinium dichloroiodate at 80; for 1 h;Inert atmosphere;

Steps:

6.7 7) Synthesis of 5,7-diiodo-8-hydroxyquinoline:
8-Hydroxyquinoline (0.1 g, 0.69 mmol) and l-butyl-3-methylpyridinium dichloroiodate (BMPDCI) (0.31 g, 0.89 mmol) were added in 10 ml of one neck round bottomed flask in an inert atmosphere and then heated at 80 °C for lhr. After the reaction was completed (TLC), ethyl acetate (10ml) was added followed by addition of water (10ml). The entire reaction mixture was extracted with ethyl acetate (3x10ml). The combined organic layers were dried using sodium sulphate and concentrated on rotavapor to afford the crude product. This was further purified by silica gel column chromatography to afford 0.24 g (87 %) of pure 5,7- diiodo-8-hydroxyquinoline as a solid. (M.P. decomposes >210 °C) 1H NMR (DMSO-d₆ δ/ppm): 8.88 (d, 1H, 7=4 Hz, Ar-H), 8.3 (s, 1H, Ar-H), 8.27-8.31 (dd, 1H, 7=1.3 Hz, 8.6 Hz, Ar-H), 7.75 (q, 1H, 7=4.2 Hz, 8.6 Hz, Ar-H).

References:

COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH;SWAMY, Vincent Paul;DESHMUKH, Amarsinh Jayawant;GORE, Pranav Sopan;THULASIRAM, Hirekodathakallu V WO2016/113757, 2016, A1 Location in patent:Page/Page column 18-19

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148-24-3 Synthesis

148-24-3
882 suppliers
$5.00/25g

83-73-8
232 suppliers
$6.00/250mg

References

148-24-3 Synthesis

148-24-3
882 suppliers
$5.00/25g

13207-63-1 Synthesis