3-Hydroxyanthranilic Acid → HCID 54244030, compound

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Reaction Steps

Thionyl chloride (25 mL) was added to 3-nitrobenzoic acid (3 g, 18.0 mmol) and the mixture was stirred at reflux for 6 hr. Thionyl chloride was evaporated under reduced pressure to give a residue which was dried in vacuum to obtain a yellow solid of 4-nitrobenzoyl chloride. 3-Hydroxyanthranilic acid (0.92 g, 6.0 mmol) and pyridine (1.45 mL, 18.0 mmol) were added to toluene (30 mL) and the mixture was stirred at room temperature for 30 min. 4-nitrobenzoyl chloride (3.34 g, 18.0 mmol) was then added. The mixture was stirred at room temperature for 30 min and then at 80° C. for 2 hr. Evaporated the solvents under reduced pressure and the residue was washed with 5% aqueous hydrochloric acid (100 mL×3), filtered, and washed with water (100 mL×3), dried in vacuum at 50° C. to obtain 3-hydroxy-2-(4-nitrobenzamido)benzoic acid (1.8 g, yield 100%) as a yellow solid. MS (ESI) m/z 303 [M+1]+.

Provenance & Evidence