Phosgene → 5-Methylisatoic anhydride

Participants

Reaction Steps

To a mixture of 10.0 g (66.0 mmol) of 5-methylanthranilic acid in 60 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 at room temperature, followed by concentration in vacuo to a small volume. The concentrated reaction mixture was filtered through silica and the filter cake was washed with hexane to give 9.81 g (83.7%) of the 5-methylisatoic anhydride as a light yellow solid. MS (Cl mode) m/z 160 (M-18, 100%), 178 (M+H, 71%).

Provenance & Evidence