Phosgene → 4-Chloroisatoic anhydride

Participants

Reaction Steps

To a mixture of 10.0 g (58.0 mmol) of 4-chloroanthranilic acid in 100 mL of 1,4-dioxane was slowly added 100 mL (193 mmol) of a 1.93 molar solution of phosgene in toluene, at room temperature. The mixture was stirred overnight. The mixture was concentrated to yield a residue which was triturated with ethyl acetate-hexane (1:4), filtered, washed with hexane and dried to afford 8.78 g (76.2%) of the 4-chloroisatoic anhydride as a light brown solid. MS (Cl mode) m/z 198 (M+H, 100%), Cl pattern 200, 35%.

Provenance & Evidence