Aniline → 3-Methyl-N-phenylbut-2-enamide

Participants

Reaction Steps

Reaction Scheme 4 illustrates the synthesis of N-isopropyl 4,4-dimethyl-2-oxo-6-aminoquinoline (Compound 34), which is used in accordance with Reaction Scheme 1 to synthesize exemplary Compound 8 of the present invention. Thus, 3,3-dimethylacryloyl chloride (Compound 35, available from Aldrich) is reacted with aniline (Compound 36) to yield N-3,3-dimethylacryloyl aniline (Compound 37). Compound 37 is ring closed under Friedel Crafts conditions to yield 4,4-dimethyl-2-oxoquinoline (Compound 38) which is thereafter alkylated with iso-propyl iodide to give N-isopropyl 4,4-dimethyl-2-oxoquinoline (Compound 39). Nitration of Compound 39 yields N-isopropyl 4,4-dimethyl-2-oxo-6-nitroquinoline Compound 40, which is reduced with hydrogen on palladium to give Compound 34.

Provenance & Evidence