Pyridine → ethyl 2-{[(2-nitrophenyl)carbonyl]amino}benzoate

Participants

Reaction Steps

A catalytic amount of DMF was added to a stirred solution of 2-nitrobenzoic acid (2.30 g, 13.8 mmol) and oxalyl chloride (6.0 mL, 69 mmol) in 1,2-dichloroethane (70 mL) at r.t. and under nitrogen flow. After 1 h, the reaction was concentrated, re-dissolved in 1,2-dichloroethane and concentrated again. The crude was immediately dissolved in 1,2-dichloroethane (25 mL) before ethyl 2-aminobenzoate (1.00 mL, 6.76 mmol) and pyridine (1.70 mL, 21.0 mmol) was added. The reaction was stirred 45 min at r.t. and under nitrogen atmosphere before being diluted with DCM and washed with HCl (aq., 1M), NaHCO3 (aq., sat., 2×) and brine. The organic phase was dried over Na2SO4, filtered, and concentrated. The crude was purified by column chromatography (SiO2, toluene:acetone 100:0→98:2) to give compound 20 in quant yield (2.24 g).

Provenance & Evidence