Trimethyl orthoformate → HCID 57447115, compound

Participants

Reaction Steps

Ethyl 3-(3-aminoquinolin-4-ylamino)-2,2-dimethylpropanoate (see Example 26 Parts A through D, 5.3 g, 18 mmol) was treated according to a modification of the method described in Part B of Example 8 using trimethyl orthoformate in lieu of trimethyl orthobutyrate. Prior to the addition of trimethyl orthoformate (3.0 mL, 27 mmol) and pyridinium p-toluenesulfonate (0.050 g), the reaction was heated at reflux for 15 minutes. The reaction was heated at reflux overnight, allowed to cool to ambient temperature, washed with saturated aqueous sodium bicarbonate (2×35 mL), and extracted with water (45 mL) containing 10% hydrochloric acid (5 mL). The acidic extract was made basic with the addition of potassium carbonate and then extracted with dichloromethane (3×50 mL). The combined organic extracts were dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide 4.3 g of ethyl 3-(1H-imidazo[4,5-c]quinolin-1-yl)-2,2-dimethylpropanoate as an oil.

Provenance & Evidence