Ethyl orthopropionate → HCID 68539371, compound

Participants

Reaction Steps

A mixture of 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy}ethanol (43.0 g, 155 mmol) and pyridine hydrochloride (1.79 g, 15.5 mmol) in toluene (200 mL) and dichloroethane (100 mL) was heated at reflux until a solution formed. The solution was allowed to cool to room temperature, then was cooled to 0° C. Triethyl orthopropionate (30.1 g, 171 mmol) was added and the mixture was heated at reflux for 3 hours. The solution was allowed to cool to room temperature and was concentrated under reduced pressure. The residue was diluted with chloroform, and 4 M NaOH was added to adjust the pH to 9. A solid formed. The mixture was filtered, and the isolated solid dissolved when it was washed with water and chloroform. The filtrate was transferred to a separatory funnel and washed twice with brine. The combined aqueous layers were back-extracted with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated to provide 40.0 g of 2-[2-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethanol as a tan solid.

Provenance & Evidence