Anthranilic Acid → 2-Azidobenzoic acid

関与物質

反応手順

Anthranilic acid (12.3 g, 90 mmol) was dissolved in a mixture of aqueous HCl (36%, 50 mL), H2O (100 mL), dioxane (50 mL) and methanol (50 mL) at 0° C. and treated dropwise with NaNO2 (7.6 g, 110 mmol) dissolved in H2O (50 ml) whereas the temperature of the reaction mixture was kept below 5° C. After 1 h at 0° C. the mixture was poured onto an icy solution of sodium acetate (26 g, 317 mmol) and sodium azide (15 g, 230 mmol) in ca. 300 ml of water. Repeated (ca. 3 times) extraction of the resulting suspension with ethylacetate, drying of the combined organic phases, and evaporation of the solvent gave (8.5 g, 58%) of 2-azido-benzoic acid. MS (ES+): 164 (M+H).

情報源と証拠