10286-77-8Relevant articles and documents
Catalyst- And oxidant-free electrochemical: para -selective hydroxylation of N -arylamides in batch and continuous-flow
Chen, Meng-Yi,Fang, Zheng,Guo, Kai,Lin, Xin-Xin,Liu, Cheng-Kou
supporting information, p. 6437 - 6443 (2020/11/09)
Hydroxyl compounds serve as key building blocks in the preparation of biologically active natural products and drugs. Traditionally, hydroxylation of the aromatic ring is achieved using stoichiometric amounts of oxidants, which leads to low atom-economy, undesired by-products, potential explosion risk and environmental pollution. Recently, electrosynthesis has attracted increasing attention as it employs clean electrical energy to promote redox reactions avoiding the use of oxidants. However, due to the poor mass and heat transfers of batch cells, low productivity and selectivity limit its further application. Herein, we develop a catalyst-, oxidant-, acidic solvent- and quaternary ammonium salt-free electrochemical para-selective hydroxylation of N-arylamides at room temperature in batch and continuous-flow. This proposal features excellent position control and water, air and functional group tolerance. Also, it is easy to scale up with higher productivity and selectivity using a flow electrolysis cell.
Novel Reactions: Part I - Facile Synthesis of Substituted ortho-Chloranilines from Nitrobenzene Derivatives
Ayyangar, N. R.,Kalkote, U. R.,Nikrad, P. V.
, p. 872 - 877 (2007/10/02)
N-Substituted benzo and acetohydroxamic acids (5), prepared from N-arylhydroxylamines and benzoyl or acetyl chloride, react readily with thionyl chloride at low temperature to give ortho-chloroanilide derivatives (6) in good yield.The latter (6) on hydrolysis give ortho-chloroanilines (10).Since the N-arylhydroxylamines are obtained from nitroarenes by partial reduction, the overall reaction amounts to the preparation of 10 from nitroarenes.
