Nitroxoline synthesis
- Product Name:Nitroxoline
- CAS Number:4008-48-4
- Molecular formula:C9H6N2O3
- Molecular Weight:190.16
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4008-48-4
8-Hydroxy-5-nitrosoquinoline (10) was oxidized to 8-hydroxy-5-nitroquinoline (11) according to the method of Petrow and Sturgeon. The procedure was as follows: finely ground 8-hydroxy-5-nitrosoquinoline hydrochloride (10) (15.0 g, 0.7 mmol) was slowly added to a 500 mL beaker containing concentrated nitric acid (45 mL) and water (30 mL) under ice bath conditions. The reaction mixture was kept continuously stirred at 17 °C for 85 min. Upon completion of the reaction, an equal volume of cold water was added and the mixture was cooled to 0°C. Subsequently, the pH was adjusted to 13.0 with cold concentrated potassium hydroxide solution to prepare the basic. The red potassium salt formed decomposed after neutralization with acetic acid and the precipitate was collected by diafiltration and washed with cold water. Finally, the residue was recrystallized from ethanol to give yellow crystals of 8-hydroxy-5-nitroquinoline. The yield was 14.10 g (90.1% yield) and the melting point was 179 °C (literature value: 179.5-181.5 °C).
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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]
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