Chloroform → 2-amino-N-(2-chlorophenyl)-4,5-dimethoxybenzamide

Participants

Reaction Steps

Prepared according to Procedure A using 4,5-dimethoxyanthranilic acid (5.0 g, 25.4 mmol) and SOCl2 (5.5 mL, 76.1 mmol) in benzene (100 mL), followed by 2-chloroaniline (6.7 mL, 63.5 mmol) and CHCl3 (75 mL). The product was washed with aqueous NaHCO3 (2×25 mL) and HCl (0.5 M, 75 mL) and purified by chromatography in CH2Cl2 to provide 4.3 g of a brown foam (55%). 1H NMR (CDCl3) δ: 8.42 (dd, J=1.5, 8.3 Hz, 1H); 8.32 (br s, 1H); 7.40 (dd, J=1.4, 8.0 Hz, 1H); 7.31 (dt, J=1.4, 7.9 Hz, 1H); 7.05 (dt, J=1.5, 7.7 Hz, 1H); 7.03 (s, 1H); 6.24 (s, 1H); 3.88 (s, 3H); 3.87 (s, 3H). MS (ES): m/z 307.0 (M+).

Provenance & Evidence