23049-93-6Relevant articles and documents
Efficient copper-catalyzed synthesis of N-alkylanthranilic acids via an ortho-substituent effect of the carboxyl group of 2-halobenzoic acids at room temperature
Zeng, Liang,Fu, Hua,Qiao, Renzhong,Jiang, Yuyang,Zhao, Yufen
supporting information; experimental part, p. 1671 - 1676 (2011/02/25)
We have developed an efficient copper-catalyzed method for the synthesis of N-alkylanthranilic acids. The protocol uses inexpensive copper(I) iodide/racemic 1,1'-binaphthyl-2,2'-diol (rac-BINOL) as the catalyst/ligand system, readily available 2-halobenzoic acids and aliphatic amines as the starting materials, the coupling reactions were performed at room temperature, and various functionalities in the substrates were tolerated.
Regioselective copper-catalyzed amination of bromobenzoic acids using aliphatic and aromatic amines
Wolf, Christian,Liu, Shuanglong,Mei, Xuefeng,August, Adam T.,Casimir, Michael D.
, p. 3270 - 3273 (2007/10/03)
A chemo- and regioselective copper-catalyzed cross-coupling procedure for amination of 2-bromobenzoic acids is described. The method eliminates the need for acid protection and produces N-aryl and N-alkyl anthranilic acid derivatives in up to 99% yield. N-(1-Pyrene)anthranilic acid has been employed in metal ion-selective fluorosensing. Titration experiments showed that this pyrene-derived amino acid forms an equimolar complex with Hg(II) in water resulting in selective fluorescence quenching even in the presence of other metal ions such as Zn(II) and Cd(II).
