Reaction Steps
1,2-diaminoanthraquinone (1.19 g, 5 mmole) was dissolved in anhydrous N, N-dimethylformamide (30 ml). Nitrogen was insufflated in the reaction flask at room temperature. Chloroacetyl chloride (0.5 ml, 6 mmole) was added into the solution. The mixture was stirred at room temperature for 2 hours. After completion of reaction, the mixture was put in an ice-water bath (200 ml), and stood still for 10 to 20 minutes to allow precipitation. The precipitate was filtered and washed with hot ethanol to obtain a red compound CC-05. Mol. Wt.: 314.7231 (C16H11N2O3); Rf: 0.82 (ethyl acetate:n-hexane=1:4); Yield: 65%; Mp.: 193-194° C. (EtOH); HRMS (EI) m/z: calcd [M]+, 314.0458 (C16H11N2O3+). Found, 314.0455. 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 4.38 (s, 2H, —CH2Cl), 7.48 (d, J=7.8 Hz, 1H, Ar—H), 7.74 (d, J=8.1 Hz, 1H, Ar—H), 7.84 (dd, J=8.1 Hz, J=1.8 Hz, 1H, Ar—H), 7.88 (t, J=1.5 Hz, 1H, Ar—H), 7.91 (dd, J=7.5 Hz, J=1.5 Hz, 1H, Ar—H), 7.96 (br, 2H, Ar—NH2), 8.14 (dd, J=7.2 Hz, J=1.8 Hz, 1H, Ar—H), 8.22 (dd, J=7.8 Hz, J=1.5 Hz, 1H, Ar—H), 9.80 (s, 1H, Ar—NH—); 13C-NMR (75 MHz, DMSO-d6) δ (ppm): 43.25, 112.98, 115.62, 126.69, 126.55, 129.88, 128.88, 128.92, 130.25, 131.01, 132.64, 133.65, 134.37, 165.72 (NCO), 182.28 (CO), 184.38 (CO).
