Hydrochloric Acid → HCID 69507061, compound

Participants

Reaction Steps

4-(7-Bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyraldehyde (2.77 g, 7.68 mmol) was dissolved in THF (75 mL), stirred at ambient temperature for 30 minutes, and cooled to 0° C. Methylmagnesium iodide (3.33 mL, 9.99 mmol, 3 M in diethyl ether) was added over 5 minutes. The reaction mixture was allowed to warm to ambient temperature. After 2 hours, 10% hydrochloric acid was added and the reaction mixture was concentrated under reduced pressure. The residue was neutralized with saturated aqueous sodium bicarbonate, extracted in 10% methanol in dichloromethane, dried over magnesium sulfate and concentrated under reduced pressure to provide 2.6 g of 5-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-ol as an orange-brown solid.

Provenance & Evidence