Hydrochloric Acid → 4-(2-Fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-(3-morpholinopropoxy)cinnoline

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A solution of 4-chloro-6-methoxy-7-(3-morpholinopropoxy)cinnoline hydrochloride (132 mg, 0.33 mmol), (prepared as described for the starting material in Example 12), and 2-fluoro-5-hydroxy-4-methylaniline (56 mg, 0.39 mmol), (prepared as described for the starting material in Example 11), in 2-pentanol (2.5 ml) containing 7M hydrogen chloride in isopropanol (9drops) was heated at reflux for 30 minutes. After cooling, the solid was filtered off, washed with isopropanol, ether and dried under vacuum to give 4-(2-fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-(3-morpholinopropoxy)cinnoline as an hydrochloride salt (yellow solid, 143 mg, 84%).

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