Ethyl orthoformate → HCID 57447025, compound

Participants

Reaction Steps

Triethyl orthoformate (12.74 mL, 76.64 mmol) and pyridinium p-toluenesulfonate (0.200 g) were sequentially added to a solution of ethyl 6-[(3-aminoquinolin-4-yl)amino]hexanoate (16.5 g, 54.7 mmol, prepared as described in Part A of Example 8) in toluene (200 mL), and the reaction was heated at reflux under a Dean-Stark trap for four hours, allowed to cool to ambient temperature, and concentrated under reduced pressure. The residue was dissolved in dichloromethane, and the resulting solution was washed sequentially with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 16.4 g of ethyl 6-(1H-imidazo[4,5-c]quinolin-1-yl)hexanoate.

Provenance & Evidence