3-Bromoaniline → 4-(3-Bromophenylamino)-7-ethoxy-6-methoxyquinoline-3-carbonitrile

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A mixture of 500 mg (1.90 mmol) 4-chloro-7-ethoxy-6-methoxy-3-quinolinecarbonitrile, 20 ml ethanol, and 250 μl (2.28 mmol) 3-bromoaniline was heated to reflux under N2. At 3 hours, added 103 μl (0.95 mmol) and 10 ml ethanol and refluxed overnight. Removed heat and made basic with saturated sodium bicarbonate. Stripped solvent, slurried residue with hexane, collected solids, and dried. Washed with water and dried in vacuo, giving 554 mg of tan solid: mass spectrum (electrospray m/e): M+H=398, 399.8.

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