31268-50-5Relevant articles and documents
Efficient copper-catalyzed N-arylations of nitrogen-containing heterocycles and aliphatic amines in water
Li, Xufeng,Yang, Daoshan,Jiang, Yuyang,Fu, Hua
experimental part, p. 1097 - 1105 (2010/08/06)
A simple and efficient copper-catalyzed method has been developed for N-arylations of nitrogen-containing heterocycles and aliphatic amines in water. The protocol uses (1E,2E)-oxalaldehyde dioxime (OADO) as the ligand, and water as the solvent, and shows good tolerance towards various functional groups.
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.
Ultrasound-promoted reaction of 2-chlorobenzoic acids and aliphatic amines
Docampo, Maite L.,Pellon, Rolando F.,Estevez-Braun, Ana,Ravelo, Angel G.
, p. 4111 - 4115 (2008/02/13)
An improvement to the use of DMF as a solvent for the condensation of 2-chlorobenzoic acids with aliphatic primary or secondary amines was described. A number of alkylaminobenzoic acids and dialkylaminobenzoic acids were synthesized in acceptable-to-good yield. The advantages of this procedure include readily available substrates, the use of an inexpensive copper powder without taking any precautions to exclude moisture under mild conditions and experimental ease. Furthermore, this condensation could also be achieved under nonclassical conditions by using ultrasonic irradiation at room temperature. We demonstrated that ultrasound-promoted condensation of 2-chlorobenzoic acid with aliphatic amines with the use of DMF as the solvent, especially in the case of secondary amines, affords products in high yields and reduces the reaction time to minutes. The results proved to be highly reproducible because the relevant sonochemical parameters were rigorously controlled. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Use of ultrasound in the synthesis of 2-(alkylamino)benzoic acids in water
Pellón, Rolando F.,Estévez-Braun, Ana,Docampo, Maite L.,Martín, Ana,Ravelo, Angel G.
, p. 1606 - 1608 (2007/10/03)
The synthesis of substituted 2-(alkylamino)benzoic acids using the Ullmann condensation with water as the solvent and utilizing ultrasound irradiation was achieved with high yields in a short reaction time. Georg Thieme Verlag Stuttgart.
