反应详情

A solution of 7-methyl-4-phenylquinoline (10.0 g, 41.7 mmol) and m-CPBA (13.5 g, 54.8 mmol) in chloroform (230 mL) was stirred at room temperature for 3 h. The reaction was quenched with saturated aqueous NaHCO3 solution and extracted twice with dichloromethane. The combined organic layers were washed with water, brine, and dried over anhydrous MgSO4. The solvent was removed under reduced pressure and the resulting crude product was dissolved in chloroform (220 mL). N,N-Dimethylcarbamoyl chloride (8.44 mL, 91.4 mmol) and trimethylsilyl cyanide (11.5 mL, 91.4 mmol) were added to this solution and stirred at room temperature for 2 d. Saturated aqueous NaHCO3 solution was added and stirred for 30 min. The organic layer was removed, and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with water, brine, and dried over anhydrous MgSO4. The solvent was removed under reduced pressure and the resulting crude product was used in the next step without further purification. 1H NMR (400 MHz, acetone-d6): δ 8.01 (s, 1H), 7.92 (d, 1H), 7.80 (s, 1H), 7.60-7.67 (m, 6H), 2.63 (s, 3H).

1. customThe reaction was quenched with saturated aqueous NaHCO3 solution
2. extractionextracted twice with dichloromethane
3. washThe combined organic layers were washed with water, brine
4. dry with materialdried over anhydrous MgSO4
5. customThe solvent was removed under reduced pressure
6. dissolutionthe resulting crude product was dissolved in chloroform (220 mL)
7. stirringstirred for 30 min
8. customThe organic layer was removed
9. extractionthe aqueous layer was extracted with dichloromethane
10. washThe combined organic layers were washed with water, brine
11. dry with materialdried over anhydrous MgSO4
12. customThe solvent was removed under reduced pressure
13. customthe resulting crude product was used in the next step without further purification