N[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[C:11]([OH:13])=[O:12].[N+]([O-])([O-])=O.[Na+].[I-:19].[K+].NC(N)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>Cl>[I:19][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[C:11]([OH:13])=[O:12]3-Aminophthalic acid (5.00 g, 27.6 mmol) was dissolved in 8.4 mol/L hydrochloric acid (60 mL), and the solution was added with an aqueous solution (10 mL) of sodium nitrate (2.0 g, 29 mmol) by drops under ice-cooling for 20 minutes, followed by stirring at the same temperature for 3 hours. Then, an aqueous solution (10 mL), in which potassium iodide (6.9 g, 41 mmol) and urea (291 mg) were dissolved, is added by drops to the mixture, followed by stirring at room temperature for 20 hours. The reaction mixture was added with 10% aqueous sodium thiosulfate solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was washed with chloroform to obtain 3-iodophthalic acid (5.0 g, yield 62%).
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