4-Aminobenzonitrile → 4-[(2-Ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino]benzonitrile

Participants

Reaction Steps

4-Aminobenzonitrile (3.47 g, 29.4 mmol) was added to a solution of 3,4-diethyoxy-3-cyclobutene-1,2-dione (5.00 g, 29.4 mmol) in absolute ethanol (100 mL). The mixture was heated at reflux overnight. The mixture was cooled, and the resulting yellow precipitate was collected by vacuum filtration. Yield: 2.60 g (37%): mp 218°-222° C.; 1H NMR (DMSO-d6): δ11.07 (s, 1H), 7.81 (d, 2H), 7.56 (d, 2H), 4.79 (q, 2H), 1.46 (t, 3H).

Provenance & Evidence