反应详情

Ethyl 3-[(3-aminoquinolin-4-yl)amino]-2,2-dimethylpropanoate (see Example 26 Parts A through D, 3.6 g, 12 mmol) was treated according to a modification of the method described in Part B of Example 8 using triethyl orthopropionate in lieu of trimethyl orthobutyrate. Prior to the addition of triethyl orthopropionate (4.0 mL, 20 mmol) and pyridinium p-toluenesulfonate (0.030 g), the reaction was heated at reflux for 15 minutes. After the reaction was heated at reflux for three hours, it was concentrated under reduced pressure and found to be incomplete by 1H NMR. The oil was dissolved in toluene (100 mL), and concentrated sulfuric acid (one drop) was added. The reaction was heated at reflux for two hours and allowed to cool. Triethylamine (5 mL) was added, and the reaction was heated at reflux for two hours, allowed to cool to ambient temperature, washed with saturated aqueous sodium bicarbonate (2×35 mL), dried over potassium carbonate, filtered, and concentrated to provide 3.6 g of ethyl 3-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2,2-dimethylpropanoate as an oil.

1. additionwas treated
2. temperaturethe reaction was heated
3. temperatureat reflux for 15 minutes
4. temperatureAfter the reaction was heated
5. temperatureat reflux for three hours
6. concentrationit was concentrated under reduced pressure
7. dissolutionThe oil was dissolved in toluene (100 mL)
8. additionconcentrated sulfuric acid (one drop) was added
9. temperatureThe reaction was heated
10. temperatureat reflux for two hours
11. temperatureto cool
12. additionTriethylamine (5 mL) was added
13. temperaturethe reaction was heated
14. temperatureat reflux for two hours
15. washwashed with saturated aqueous sodium bicarbonate (2×35 mL)
16. dry with materialdried over potassium carbonate
17. filtrationfiltered
18. concentrationconcentrated