Methyl Anthranilate → Methyl 2-(3-chloro-4-methoxybenzamido)benzoate

Beteiligte Stoffe

Reaktionsschritte

A solution of methyl 2-aminobenzoate (500 mg, 3.3 mmol) (Aldrich Chemical Co., Milwaukee, Wis.) and 3-chloro-4-methoxybenzoic acid (645 mg, 3.3 mmol) (Lancaster Synthesis Ltd., Windham, N.H.) in DMF (20 mL) was treated with EDCI (1.3 g, 6.6 mmol) and DMAP (800 mg, 6.6 mmol) at room temperature. The reaction mixture was stirred for 24 hours, and then concentrated. The crude residue was dissolved in EtOAc (50 mL) and washed with 0.1 N HCl (2×20 mL), saturated aqueous NaHCO3 (2×20 mL). The organic layer was dried (Na2SO4), filtered, and concentrated. The crude product was purified by chromatography (SiO2, 15% EtOAc in hexanes) to afford 42A as a white solid (350 mg, 33%).

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