Hydrochloric Acid → 5-Iodo-2-(methylamino)benzoic acid

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In a 1 L beaker was placed 40 grams (0.267 mmol) of N-methylanthranilic acid dissolved in 300 mL water and 26.7 mL conc. HCl cooled to 20° C. A solution of ICL, prepared by dissolving 44 grams of ICl to a cooled (0° C.) solution of 167 mL water and 45 ml conc. HCl, was rapidly added to the stirred N-methylanthranilc acid solution. The reaction was allowed to stir for 2 hrs, filtered on a medium glass frit funnel, washing the solids with water. The green powder isolated was dried under vacuum to yield 70 grams (96%) of 5-iodo-N-methylanthranilic acid. 1H NMR (DMSO-d6) 7.61 (1H, bs, C6-H), 7.21 (1H, bd, 3JHH =8 Hz, C4-H), 6.19 (1H, d, 3JHH =8 Hz, C3-H), 2.43 (3H, s, NCH3); 13C NMR (DMSO-d6) 169.0, 151.4, 142.7, 139.6, 114.2, 112.7, 74.2, 29.6.

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