[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=[N:4][CH:3]=1.[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([Cl:1])=[CH:3][N:4]=[N:5]2)=[CH:10][CH:9]=1A solution of 4-chloro-7-methylcinnoline (0.6 g, 3.37 mmol) in carbon tetrachloride (30 mL) is treated with N-bromosuccinimide (0.64 g, 3.4 mmol) and a catalytic amount of 70% benzoyl peroxide (0.22 g, 0.63 mmol). The solution is heated to 80° C. overnight, then filtered. The filtrate is concentrated in vacuo and the resulting residue is chromatographed (20% ethyl acetate/methyl chloride) to give the title compound (0.3 g, 1.2 mmol) and some unreacted starting material (0.1 g, 0.56 mmol). MS m/z: [M+H]+=257; 1H NMR (CDCl3, 300 MHz) δ9.35 (s, 1H), 8.55 (s, 1H), 8.2 (d, 1H), 8.85 (d, 1H), 4.75 (s, 2H).
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