Nitric Acid → HCID 135838168, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of fuming nitric acid (7 ml) and sulphuric acid (6 ml) at 0° C. was added 1,3-diamino-8-bromo-5,6-dihydrobenzo[f]quinazoline (1.0 g, 3.4 mmoles) in a single portion. The reaction mixture was stirred at 0-5° C. for 45 minutes, and then slowly poured onto ice (15 g). The resulting precipitate was filtered, washed with water (10 ml) and ether (10 ml), and resuspended in boiling 1N HCl (100 ml) for 1 hour. After cooling, the solid was filtered, triturated with hot ethanol, filtered again, washed with ethanol and ether, and dried to give 3-amino-8-bromo-9-nitrobenzo[f]quinazolin-1(2H)-one as a pale yellow solid. (0.59 g, 45%) 1H NMR (DMSO-d6, 80 MHz) δ: 7.62-7.71 (d, J=7 Hz, 1H, Ar); 7.77 (s, 3H, NH3+); 8.23-8.34 (d, J=9 Hz, 1H, Ar); 8.59 (s, 1H, Ar); 10.08 (s, 1H, Ar). Anal. Calculated for C12H7BrN4O3.1/2HNO3.H2O C, 37.47; H, 2.49; N, 16.39. Found C, 37.20; H, 2.24; N, 16.00.

Provenance & Evidence