1,2-Dichloroethane → HCID 3010836, compound

Participants

Reaction Steps

4-Oxo-1,4-dihydro-3-cinnolinecarboxylic acid (0.10 g, 0.53 mmol) is dissolved in 5 mL DMF. To this is added 4-chlorobenzylamine (0.07 ML, 0.58 mmol) and the reaction mixture is stirred at room temperature for 5 min. EDC (0.11 g, 0.57 mmol) and HOBt (0.08 g, 0.56 mmol) are added and the reaction is stirred at room temperature over 2 days. The mixture is poured into 30 mL H2O. A brown precipitate formed which is filtered. The crude product is triturated with hot EtOAc, filtered and dried to yield 0.012 g (7%) of the desired product. Physical characteristics are as follows: m.p. 269-271° C.; 1H NMR (300 MHz, DMSO) δ 14.2, 10.0, 8.17, 7.87, 7.74, 7.56, 7.38, 4.53; MS (fab) m/z 314 (M+H)+, 316, 315, 299, 298, 297, 127, 125, 123, 58.

Provenance & Evidence