Homophthalic anhydride → 3-(1,3-dioxo-3,4-dihydroisoquinolin-2(1H)-yl)-N-cyclopropyl-4-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

A suspension of 1H-isochromene-1,3(4H)-dione (400 mg) and 3-amino-N-cyclopropyl-4-methylbenzamide (514 mg) in toluene (3 ml) was heated under microwave irradiation conditions (Personal Chemistry Emrys Optimizer with 300 W magnetron) at 150° C. for 60 minutes. The reaction mixture was diluted with ethyl acetate and washed with 2N HCl, water, brine, dried (magnesium sulfate) and concentrated to a foam which was purified by column chromatography with a gradient of iso-hexane to 70% ethyl acetate/iso-hexane to yield 3-(1,3-dioxo-3,4-dihydroisoquinolin-2(1H)-yl)-N-cyclopropyl-4-methylbenzamide as a solid (464 mg); NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.69 (m, 2H), 2.09 (s, 3H), 2.85 (m, 1H), 4.33 (d, 1H), 4.41 (d, 1H), 7.42 (d, 1H), 7.49-7.55 (m, 2H), 7.65 (s, 1H), 7.74 (t, 1H), 7.80 (d, 1H), 8.09 (d, 1H), 8.39 (d, 1H); Mass Spectrum: M+H+ 335.

Provenance & Evidence