Aniline → 2-Propenoic acid, 2-cyano-3-(phenylamino)-, ethyl ester, (E)-

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Reaction Steps

0.91 ml (10 mmol) of aniline and 1.69 g (10 mmol of ethyl(ethoxymethylene)cyanoacetate were dissolved in 10 ml of pyridine and heated under reflux. After 3 h pyridine was removed under vacuum, and the residue was purified by chromatography (silica gel column, eluent 1% methanol in dichloromethane). 1.08 g (50%) of ethyl(anilinomethylene)cyanoacetate were obtained. The compound was cyclized by heating in a biphenyl/phenyl ether mixture. After cooling a precipitate was filtered and washed with diethyl ether to give 4-hydroxyquinoline-3-carbonitrile (49%). Following the procedure outlined in Step 3 of Example 1, but substituting 4-hydroxyquinoline-3-carbonitrile for 9-(10H)acridone, 4-chloro-3-cyanoquinoline (90%) was obtained, which was reacted with 4-(4-methylpiperazin-1-yl)aniline (according to the procedure of Step 4 in Example 1), to afford the title compound with 12% yield (overall yield 3%).

Provenance & Evidence