Anthranilic Acid → 2-(Octanoylamino)benzoic acid
Reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].N1C=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-].Cl.[O:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>>[C:20]([NH:4][C:3]1[C:2](=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:1]([OH:10])=[O:9])(=[O:19])[CH2:21][CH2:22][CH2:23][CH2:12][CH2:13][CH2:14][CH3:15]Participants
6
Procedure
Anthranilic acid was dissolved in a mixed solvent containing pyridine and tetrahydrofuran (THF) in 5:5 ratio and a THF solution of n-caprioyl chloride was dropped to the solution during several hours for reaction. After the reaction, hydrochloric acid was added to the reaction mixture. Pyridine hydrochloride was filtered and the solvent was removed. N-n-octanoylanthranilic acid was obtained from the remaining reactant after the purification by column chromatography with the yield of 79.4%.