Hydrochloric Acid → HCID 14442113, compound

Participants

Reaction Steps

To a 500 ml round-buttomed flask equipped with condenser and N2 inlet are added 15.7 g (0.10 mol) 2-chlorobenzoic acid, 23.3 g (0.17 mol) 3-aminobenzoic acid, 23.5 g (0.17 mol) potassium carbonate, 50 mg copper powder, and 40 ml dimethylformamide. The mixture is heated to reflux, and three 50 mg portions of methanol-washed copper #(I) bromide are added. The reaction is refluxed 3.5 hours, cooled, and poured into 1 1 1N HC1. The mixture is stirred for 10 minutes, filtered, and the filtered solid washed with water, methanol, and ether, and dried to afford a gray solid, mp 277°-279° C., 19 g (73.9%). The acid is taken up in 250 ml methanol, the solution is saturated with HCl and refluxed 40 hours, and cooled and evaporated. The residue is chromatographed on silica gel using methylene chloride as eluent to afford 17.46 g (61.3% overall) of a yellow oil. NMR (d, CDC13): 3.97 (s, 3H), 6.7-8.0 (m, 8H). IR (Cm.-1, KBr): 1730 (C=O).

Provenance & Evidence