[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:10])[C:8]=1[Cl:9])[NH2:5].Cl.[N:12]([O-])=O.[Na+].[O:16]=[C:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1C(O)=O>O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][N:12]=[C:18]2[CH2:19][CH2:20][CH2:21][CH2:22][C:17]2=[O:16])[CH:6]=[C:7]([Cl:10])[C:8]=1[Cl:9]3,4,5-Trichloroaniline (1.6 g, 11.2 mmol) was dissolved in water (4 mL), cooled to 0° C., conc. HCl (1.5 ml) followed by a solution of NaNO2 (0.7 g, 11.2 mmol) in water (4 mL), was added dropwise and the resulting mixture was stirred for 30 min. followed by the addition of a solution of 2-oxocyclohexanecarboxylic acid. The reaction mixture was warmed to room temperature and stirred for 1 h during which time a solid precipitated out which was filtered and air dried to give the title compound (1.0 g, 29%). 1H NMR (500 MHz, CDCl3, δ in ppm) 13.5 (bs, 1H), 7.26 (s, 2H), 2.70 (s, 2H), 2.53 (s, 2H), 1.87 (s, 4H).
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