Hydrochloric Acid → 6-Amino-4-(3-chloro-4-(pyrid-2-ylmethoxy)phenylamino)-7-ethoxyquinoline-3-carbonitrile

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Reaction Conditions

Reaction Steps

A mixture of N-(4-chloro-3-cyano-7-ethoxyquinolin-6-yl)acetamide (11.64 g, 0.04 mol, 1.00 equiv), 3-chloro-4-(pyridin-2-ylmethoxy)aniline (9.53 g, 0.04 mol, 1.00 equiv), methanesulfonic acid (1.3 ml, 0.02 mol, 0.5 equiv) in ethanol (30 ml) was stirred under refluxed for 6 hours and then 0.6N hydrogen chloride (600 ml, 0.36 mol) was added. The mixture was heated to 80° C. for additional 19 hours, and then cooled to 0° C. where the precipitated solids were formed and filtered. The product was added to a solution of 1N potassium carbonate (200 ml, 0.2 mol) in methanol (300 ml) and the resulting mixture was stirred for 3 hours. The resulting precipitated solids were filtered, washed with 1:1 methanol/water (500 ml) and dried to give 12.8 g of product. MS (ESI) m/z: 446 (M+1).

Provenance & Evidence