1,1,1-Trimethoxybutane → HCID 57447018, compound

Participants

Reaction Steps

Trimethyl orthobutyrate (15.0 g, 49.8 mmol) and pyridinium p-toluenesulfonate (0.20 g, 0.80 mmol) were added to a solution ethyl 6-[(3-aminoquinolin-4-yl)amino]hexanoate (15.0 g, 49.8 mmol) in toluene (400 mL), and the reaction was heated at reflux under a Dean-Stark trap for 4.5 hours while the distillate was periodically removed. The reaction was allowed to cool to ambient temperature, washed sequentially with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide ethyl 6-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)hexanoate, which was used without purification.

Provenance & Evidence