N[C:2]1[C:3]([Cl:18])=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13])[NH:8][C:7](=[O:16])[C:6](=[O:17])[NH:5]2.N([O-])=O.[Na+].[ClH:23]>OS(O)(=O)=O.O.Cl[Cu]>[Cl:18][C:3]1[C:2]([Cl:23])=[C:11]([C:12]([F:15])([F:14])[F:13])[CH:10]=[C:9]2[C:4]=1[NH:5][C:6](=[O:17])[C:7](=[O:16])[NH:8]2A mixture of 25 mg (0.089 mmol) of 6-amino-5-chloro-7-trifluoromethyl-1,4-dihydroquinoxaline-2,3-dione in 1 mL of concentrated H2SO4 (97%) was stirred in an ice-bath for 1 h. To the resulting yellow solution was added dropwise solution of 40 mg (0.58 mmol) of NaNO2 in 0.5 mL of H2O and the solution was stirred in an ice-bath for 2 h. To the resulting red solution was added an icy cooled solution of 60 mg of CuCl in 0.8 mL of 6N HCl and the resulting mixture was stirred in ice-bath for 2 h, then at room temperature overnight. The mixture was diluted by 2 mL of H2O and stirred for 1 h, then 2 mL of H2O and stirred for 1 h. It was filtered, washed by water, and dried to leave white solid (20 mg, 74%), mp>250° C. 1H NMR (DMSO-d6), 7.492 (s, 1), 11.849 (mb, 1), 12.229 (s, 1). MS, 298 (M+, 100), 270 (85), 207 (40), 173 (60). HRMS Calcd for C9H335Cl2F3N2O2, 297.9520, found 297.9520.
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