Nitroxoline synthesis
- Product Name:Nitroxoline
- CAS Number:4008-48-4
- Molecular formula:C9H6N2O3
- Molecular Weight:190.16
63450-86-2
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Yield:4008-48-4 90.1%
Reaction Conditions:
with nitric acid in water at 17; for 1.41667 h;Inert atmosphere;Cooling with ice;
Steps:
Synthesis of 8-hydroxy-5-nitroquinoline (11)
The oxidation of 8-hydroxy-5-nitrosoquinoline (10) to 8-hydroxy-5-nitroquinoline(11 ) was carried out according to the procedure ofPetrow and Sturgeon20. Finely grounded 8-hydroxy-5-nitrosoquinoline hydrochloride (10) (15.0 g, 0.7mmol) was added into a 500 mL beaker containingconcentrated nitric acid (45 mL) and water (30 mL)in an ice bath. The mixture was stirred for 85 min at17 °C. Equal volume of cold water was added andthe mixture cooled to 0 °C and alkaline was madewith cold concentrated potassium hydroxidesolution pH 13.0. The red potassium salt wasdecomposed on neutralization with acetic acid,filtered by suction and washed with water. Theresidue was recrystallized from ethanol to afford abright yellow crystal of 8-hydroxy-5-nitroquinoline.Yield 14.10 g (90.1%), mp 179 °C (lit 179.5-181.5°C)20.
References:
Oni, Timothy Toba;Okoro, Uchechukwu Chris;Ugwu, David Izuchukwu [Oriental Journal of Chemistry,2015,vol. 31,# 1,p. 371 - 378]
148-24-3
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3565-26-2
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19746-57-7
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4008-48-4
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