Nitric Acid → HCID 19990462, compound

Participants

Reaction Steps

To 75 ml ice-cooled 100% nitric acid was added gradually 8.1 g (32.1 mmol) 2-chloro-5-ethoxalylaminobenzonitrile. Stirring was continued at 0° C. for 1.5 h, and then the reaction mixture was poured into 500 ml ice-water. The precipitated product was filtered off and recrystallized (ethanol-water) to give 8.25 g (86%) of 6-chloro-3-ethoxalylamino-4-nitrobenzonitrile. M.p. 143-45° C. 1H-NMR (CDCl3 -DMSO-d6): 11.3 (1H, broad s), 8.1 (2H, dd, J=10 Hz), 4.3 (2H, q), 1.4 (3H, t). The filtrate was extracted with 150 ml ethylacetate to give 2-chloro-3-ethoxalylamino-4-nitrobenzonitrile as an oil (0.67 g, 7%). 1H-NMR (CDCl3 -DMSO-d6) 11.4 (1H, broad s), 8.57 (1H, s), 8.33 (1H, s), 4.3 (2H, q), 1.4 (3H, t).

Provenance & Evidence