反应详情

温度

70 °C

6-Methoxy-8-nitroquinoline (1 mmol) (scheme 1) was dissolved in CH3CN (5 mL) while reaction mixture was warmed to 70° C. Silver nitrate (0.6 mmol), trimethylacetic acid (2.5 mmol), and 10% H2SO4 (10 mL) was then added to the reaction mixture. A freshly prepared solution of ammonium persulfate (3 mmol) in water (10 mL) was added drop wise to the pre-heated (70° C.) mixture during 10 minutes. The heating source was then removed and reaction proceeded with evolution of carbon dioxide. After 10 minutes, reaction mixture was poured onto ice, and resulting mixture was made alkaline with addition of 30% NH4OH. Extracted with ethyl acetate (4×50 mL), and combined extracts were washed with NaCl solution (2×10 mL). Dried over Na2SO4 and solvent removed in vacuo to afford oil, which on flash column chromatography over silica gel (230-400 mesh) gave 2-tert-Butyl-6-methoxy-8-nitroquinoline in good yield.

1. customwhile reaction mixture
2. temperaturepre-heated (70° C.) mixture during 10 minutes
3. customThe heating source was then removed
4. customreaction
5. customreaction mixture
6. additionwas poured onto ice
7. customresulting mixture
8. extractionExtracted with ethyl acetate (4×50 mL)
9. washwere washed with NaCl solution (2×10 mL)
10. dry with materialDried over Na2SO4 and solvent
11. customremoved in vacuo
12. customto afford oil, which on flash column chromatography over silica gel (230-400 mesh)