Anthranilic Acid → 3,4-Dihydro-4-oxo-2-quinazolineacetonitrile

Participants

Reaction Steps

2-Cyanoethanethioamide (1.00 g, 10.0 mmol) and bromoethane (821 μL, 11.0 mmol) were added to an ethanolic solution of sodium ethoxide (11.5 mmol, 5.3 mL). The resulting mixture was stirred for 6 hours, 2-aminobenzoic acid (1.50 g, 10.9 mmol) was added, and the reaction was refluxed overnight with stirring. A solid precipitate formed upon cooling of the reaction mixture, which was recovered by vacuum filtration and washed sequentially with ethanol, water, ethanol, and diethyl ether. The solid was then dried to yield 2-(4-oxo-3,4-dihydroquinazolin-2-yl)acetonitrile (872 mg, 47%). 1NMR (400 MHz, DMSO-d6) δ ppm 4.17 (s, 2H), 7.53 (t, J=7.5 Hz, 1H), 7.68 (d, J=7.9 Hz, 1H), 7.83 (t, J=7.8 Hz, 1H), 8.10 (dd, J1=7.9 Hz, J2=1.2 Hz, 1H).

Provenance & Evidence