Sodium Bicarbonate → HCID 57447110, compound

Participants

Reaction Steps

A neat mixture of N-(4-chloroquinolin-3-yl)butanamide (5.0 g, 20 mmol) and glycine ethyl ester hydrochloride (10.0 g, 72 mmol) was heated gently with a heat gun until the solids melted. The reaction was followed by LC/MS, and heat was applied briefly twice more until no starting material remained. Dichloromethane (100 mL) and saturated aqueous sodium bicarbonate (50 mL) were added, and the resulting mixture was stirred until all solids were dissolved. The aqueous layer was separated and extracted with dichloromethane (2×50 mL), and the combined organic fractions were washed sequentially with saturated aqueous sodium bicarbonate (50 mL) and water, dried over potassium carbonate, filtered, and concentrated under reduced pressure. The residue was (3.6 g) was dissolved in hot toluene (150 mL), and pyridinium tosylate (100 mg) was added. The reaction was heated at reflux under a Dean-Stark trap for one hour, allowed to stand at ambient temperature for three days, heated at reflux for two hours, cooled to ambient temperature, and diluted with dichloromethane (150 mL). The resulting solution was washed with saturated aqueous sodium bicarbonate (2×35 mL), dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide 3.2 g of ethyl (2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)acetate as a light brown solid.

Provenance & Evidence