Hydrochloric Acid → HCID 86732727, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of ethyl 3-hydroxy-1-methyl-4-oxo-1,4-dihydroquinoline-6-carboxylate (6.7 g, 27.1 mmol) in N,N-dimethylformamide (18.0 ml) at 0° C. was added sodium hydride (2.168 g, 54.2 mmol), and the mixture was stirred for 20 min. At this time, 1-(chloromethyl)-4-methoxybenzene (3.7 ml, 27.3 mmol) was added and the reaction was heated to 75° C. and allowed to stir for 2 h. After cooling, the reaction was poured into ice, and the resulting precipitate was filtered, washed with water and diethyl ether, collected, and dried. Methanol (24.00 ml), water (8.00 ml) and lithium hydroxide (0.86 g, 35.9 mmol) were added, and the reaction was stirred at 60° C. for 2 h. The reaction was cooled and the pH was adjusted to 3-4 by addition of 2N hydrochloric acid (18.00 ml, 36 mmol). The resulting precipitate was filtered, washed with water and diethyl ether, and dried to give 3-((4-methoxybenzyl)oxy)-1-methyl-4-oxo-1,4-dihydroquinoline-6-carboxylic acid (6.1937 g, 18.25 mmol, 67.4% yield. LCMS: (M+H)+: 340.1.

Provenance & Evidence