Title compound has been prepared by two synthetic ways: 1) Condensation of the acetoacetanilide (I) with triethyl orthoformate in the presence of Ac2O provided the ethoxymethylene compound (II), which was reacted with hydroxylamine in methanol-water to afford isoxazole (III). Ring opening of the heterocycle with NaOH then gave the target cyanoacetanilide. 2) In a different procedure, cyanoacetic acid (V) was coupled with 2,5-dibromoaniline (IV) in the presence of diisopropyl carbodiimide (DIC) to form cyanoacetanilide (VI), which was acylated using acetyl chloride and NaH to afford the hydroxyethylidene derivative.
Two synthetic ways have been reported for the compound. Coupling of cyanoacetic acid (II) to 4-(trifluoromethoxy)aniline (I) in the presence of diisopropylcarbodiimide formed the cyanoacetamide (III), which was treated with NaH and then acylated with acetyl chloride to yield the title compound.
Alternatively, aniline (I) was coupled with 5-methylisoxazole-4-carbonyl chloride (IV) to provide the isoxazolecarboxamide (V). The isoxazole ring was then opened with NaOH to furnish the target cyanopropenamide.