2-Chloro-3'-nitrobenzanilide synthesis

Yield:-

Reaction Conditions:

with triethylamine in acetonitrile at 75; for 3 h;

Steps:

Step 1, preparation of 3-methyl-N-(3-nitrophenyl)benzamide:

General procedure: To a vial containing acetonitrile (10mL) was added 3-nitroaniline (0.50g, 3.62mmol), NEt₃ (0.56mL, 3.98mmol), and 3-methylbenzoyl chloride (0.50mL, 3.80mmol). The vial was capped, and the resulting solution was heated at 75°C for 3h. After cooling to room temperature, the solution was concentrated, the residue was dissolved in CH₂Cl₂ (10mL) and then it was washed with saturated aqueous NaHCO₃ (2×5mL). The separated organic extract was dried (MgSO₄), filtered and adsorbed onto silica. Purification by MPLC (0-30% EtOAc/hexanes) afforded 3-methyl-N-(3-nitrophenyl)benzamide (0.86g, 3.36mmol, 93% yield) as an off-white solid.

References:

Flaherty, Daniel P.;Simpson, Denise S.;Miller, Melissa;Maki, Brooks E.;Zou, Beiyan;Shi, Jie;Wu, Meng;McManus, Owen B.;Aubé, Jeffrey;Li, Min;Golden, Jennifer E. [Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,# 16,p. 3968 - 3973]