تفاعل #577102

معادلة التفاعل

ammonium persulfate

NH4OH

1-adamantanecarboxylic acid

H2SO4

carbon dioxide

6-Methoxy-8-nitroquinoline

→

2-adamantyl-6-methoxy-8-nitroquinoline

المردود 70.0%

المذيبات

water

CH3CN

ظروف التفاعل

المعالجة

1. 1
   أخرىwhile reaction mixture
2. 2
   درجة الحرارةpre-heated (70° C.) mixture during 10 minutes
3. 3
   أخرىThe heating source was then removed
4. 4
   أخرىreaction
5. 5
   أخرىreaction mixture
6. 6
   workup.ADDITIONwas poured onto ice
7. 7
   أخرىresulting mixture
8. 8
   استخلاصExtracted with ethyl acetate (4×50 mL)
9. 9
   غسيلwere washed with NaCl solution (2×10 mL)
10. 10
    تجفيفDried over Na2SO4 and solvent
11. 11
    أخرىremoved in vacuo
12. 12
    أخرىto afford oil, which on flash column chromatography over silica gel (230-400 mesh)

الإجراء التجريبي

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), 1-adamantanecarboxylic acid (2 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-adamantyl-6-methoxy-8-nitroquinoline in good yield.

المصدر