反应详情

To a solution of 4-nitrophenol (7.2 g, 52.0 mmol) in 400 mL THF was added 4-(chloromethyl)-2-methylquinoline (10.0 g, 52.0 mmol), cesium carbonate (25.4 g, 78 mmol), and sodium iodide (451 mg, 3 mmol). The reaction was heated to reflux for 24 hr, after which the reaction was extracted from sat KH2PO4 with EtOAc×3. The combined organic layers were dried with MgSO4, filtered, and concentrated. This residue was taken up in 200 mL MeOH and refluxed with SnCl2 (156 mmol) for 18 hr after which, the solution was cooled and the reaction was extracted from disodium tartrate with EtOAc×4, the combined organic layers were dried with MgSO4, filtered, and concentrated. The residue was treated with 2 M HCl in dioxane, rotovapped, and recrystallized from EtOH/water to give 12.4 g (71%). MS found: (M+H)=265.

1. temperatureThe reaction was heated
2. temperatureto reflux for 24 hr
3. extractionafter which the reaction was extracted
4. dry with materialThe combined organic layers were dried with MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. temperaturethe solution was cooled
8. extractionthe reaction was extracted from disodium tartrate with EtOAc×4
9. dry with materialthe combined organic layers were dried with MgSO4
10. filtrationfiltered
11. concentrationconcentrated
12. additionThe residue was treated with 2 M HCl in dioxane
13. customrecrystallized from EtOH/water
14. customto give 12.4 g (71%)