39614-85-2Relevant articles and documents
Br?nsted acid-catalyzed chlorination of aromatic carboxylic acids
Yu, Zhiqun,Yao, Hongmiao,Xu, Qilin,Liu, Jiming,Le, Xingmao,Ren, Minna
supporting information, p. 685 - 689 (2021/04/09)
The chlorination of aromatic carboxylic acids with SOCl2 has been effectively performed by reacting with a Br?nsted acid as the catalyst. Based on this discovery, an efficient catalytic method that is cheaper than traditional catalytic methods was developed. 20 substrates were chlorinated offering excellent yields in a short reaction time. And the SOCl2/Br?nsted acid system has been used in a larger scale preparative reaction. A dual activation mechanism was proposed to prove the irreplaceable system of SOCl2/Br?nsted acid.
An atom economical method for the direct synthesis of quinoline derivatives from substituted o-nitrotoluenes
Liu, Guiyan,Yi, Maocong,Liu, Lu,Wang, Jingjing,Wang, Jianhui
, p. 2911 - 2914 (2015/02/19)
A highly efficient one-pot procedure for the preparation of substituted quinolines from substituted o-nitrotoluenes with electron-withdrawing groups and olefins (acrylic esters and acrylonitriles) using a cesium catalyst has been developed. A plausible [2+4] cycloaddition mechanism is proposed. This method uses nitroaromatic compounds as the starting materials to give quinoline derivatives in good to high yields under mild conditions with no transition metal catalysis. It provides an atom economical pathway for the synthesis of quinoline derivatives which could be used in industrial processes.
A reevaluation of the Hofmann rearrangement in electron deficient systems: Preparation of 2-(15N)amino-4,6-dinitrotoluene and 4-(15N)- amino-2,6dinitrotoluene
Spanggord, Ronald J.,Clizbe, Lane A.
, p. 615 - 621 (2007/10/03)
The Hofmann rearrangement is an excellent synthetic method to introduce amino functions into aromatic molecules; however, it becomes less efficient in electron-deficient systems because of competitive hydrolytic reactions. This report describes the preparation of the aminodinitrotoluenes (ADNTs) 2- (15N)amino-4,6-dinitrotoluene and 4-(15N)-amino-2,6-dinitrotoluene by developing conditions using HPLC as a reaction monitoring technique. Both ADNTs were prepared in >70% yield and >95% isotopic purity by using organic solvents and controlling pH during the formation of N-chlorobenzamides and then performing the rearrangement.