Ethyl 5-methoxyimidazo[1,2-a]quinoline-2-carboxylate → HCID 13055757, compound

A suspension of 19.71 g (73 mmol) of ethyl 5-methoxyimidazo[1,2-a]quinoline-2-carboxylate in 350 ml of freshly distilled anhydrous tetrahydrofuran was stirred under a nitrogen atmosphere at room temperature and 3.33 g (88 mmol) of lithium aluminum hydride were added thereto in portions over 3 hours. The mixture was stirred for 4 hours and excess hydride was destroyed by dropwise addition of wet tetrahydrofuran followed by water. The mixture was poured into 1.5 liters of water and the mixture was extracted with 500 ml of a chloroform-methanol mixture. The mixture was filtered through a celite pad and the aqueous phase was extracted again with a chloroform-methanol mixture. The combined organic phases were dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure. The residue was triturated with ethyl acetate, filtered, washed with ethyl acetate and dried under reduced pressure over P2O5 to obtain 14.87 g (89% yield) of 5-methoxy-imidazo[1,2-a]quinoline-2-methanol as a white crystalline solid melting at 173°-175° C.