Water → AURORA 623

Participants

Reaction Steps

4-Nitrobenzenesulfonyl chloride (2.22 g, 10 mmol) is added to a solution of methyl anthranilate (1.51 g, 10 mmol) in 20 mL of DCM at RT, followed by slow addition of pyridine (0.97 mL, 12 mmol). The reaction is stirred 16 h at RT. Water (1 mL) is added. After 1 h, the mixture is partitioned between DCM (40 mL) and water (30 mL). The organic phase is washed with water (30 mL) and brine (30 mL), dried over anhydrous magnesium sulfate and concentrated under vacuum to an orange solid. The solid is redissolved in DCM (30 mL), and hexane (100 mL) is added. The solution is concentrated to approximately 60 mL at which point an orange solid rapidly precipitated. The solid is collected by filtration and dried under vacuum to give 2-(4-nitro-benzenesulfonylamino)-benzoic acid methyl ester.

Provenance & Evidence