HCID 15735723, compound → 2-[[2-Chloro-3-(1-hydroxyethyl)phenyl]amino]benzoic acid
Reaction equation
C1C=CC([I+][C:8]2[C:13]([C:14]([O-:16])=[O:15])=[CH:12][CH:11]=[CH:10][CH:9]=2)=CC=1.O.[NH2:18][C:19]1[C:20]([Cl:28])=[C:21]([CH:25]([CH3:27])[OH:26])[CH:22]=[CH:23][CH:24]=1>C(O)(C)C>[Cl:28][C:20]1[C:21]([CH:25]([OH:26])[CH3:27])=[CH:22][CH:23]=[CH:24][C:19]=1[NH:18][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=1[C:14]([OH:16])=[O:15]Participants
4
Procedure
A mixture of diphenyliodonium-2-carboxylate monohydrate (11.4 g, 33.3 mmol), 3-amino-2-chloro-α-methylbenzenemethanol (5.2 g, 30.3 mmol), and cupric acetate (0.5 g) in isopropanol (100 mL) is heated at reflux for 12 hours under an argon atmosphere. The solvent is evaporated under vacuum and the remaining dark oil is taken up in 10% aqueous KOH. The insoluble material is removed by filtration through Celite-545, and the filtrate is extracted with ether to remove nonacidic impurities. The aqueous solution is acidified to pH=3 with concentrated HCl. The resulting precipitate is collected by filtration and purified by column chromatography (silica, ethyl acetate) to give pure 2-[[2-chloro-3-(1-hydroxyethyl)phenylamino]benzoic acid (5.8 g, 60%), mp=169-171° C.