52723-84-9

Usage

InChI:InChI=1/C15H14ClNO2/c1-11-9-12(16)7-8-14(11)19-10-15(18)17-13-5-3-2-4-6-13/h2-9H,10H2,1H3,(H,17,18)

Upstream product

• 2698-38-6 ethyl 2-(4-chloro-2-methylphenoxy)acetate 
• 62-53-3 aniline 
• 98-95-3 nitrobenzene 

Downstream Products

• 5866-70-6 [2-(4-Chloro-2-methyl-phenoxy)-acetyl]-phenyl-carbamic acid isopropyl ester 

Relevant academic research and scientific papers

Chromium-catalyzed ligand-free amidation of esters with anilines

Amides are important structural motifs in pharmaceutical and agrochemical chemistry because of the intriguing biological active properties. We report here the amidation of commercially available esters with anilines that was promoted by low-cost and air-stable chromium(III) pre-catalyst combined with magnesium, providing access to amides. This reaction occurs without the use of external ligands in a simple operation. Mechanistic studies indicate that a reactive aminated Cr species responsible for the amidation can be considered, which may be formed by reaction of low-valent Cr with aniline followed by reduction with hydrogen evolution.

Chromium-Catalyzed Activation of Acyl C-O Bonds with Magnesium for Amidation of Esters with Nitroarenes

Here, we report a chromium-catalyzed activation of acyl C-O bonds with magnesium for amidation of esters with nitroarenes. Low-cost chromium(III) chloride shows high reactivity in promoting amidation by using magnesium as reductant and chlorotrimethylsilane as additive. It provides a step-economic strategy to the synthesis of centrally important amide motifs using inexpensive and air-stable nitroarenes as amino sources.