Dimethylformamide → (4E)-4-(Methoxymethylene)-6-nitroisoquinoline-1,3(2H,4H)-dione

Participants

Reaction Steps

To a stirred mixture of 0.41 g (2.0 mmol) of 6-nitroisoquinoline-1,3(2H,4H)-dione, 3.2 ml (34 mmol) of Ac2O, and 0.80 ml of N,N-dimethylformamide is added 0.44 ml (4.0 mmol) of trimethyl orthoformate. The mixture is heated to 125° and maintained for 30 m, cooled, diluted with ether, and stirred for 10 m. The resulting brown solid is filtered, washed with ether, and dried to give 372 mg (74%); 1H NMR (DMSO-d6) δ 11.55 (s, 1H), 8.99 (d, J=2.0 Hz, 1H), 8.30 (d, J=8.6 Hz, 1H), 8.19 (dd J=2.0, 8.6 Hz, 1H), 4.33 (s, 3H).

Provenance & Evidence