Friedel–Crafts Alkylation of N‐(2‐Chloropropionyl)aniline and the Generation Mechanism of Byproducts

Abstract

in Wiley Online Library (wileyonlinelibrary.com).The cyclization of N-(2-chloropropionyl)aniline to 3-methylindolin-2-one through Friedel-Crafts alkylation was studied. It was found that N-phenylacrylamide (12.6%) and 3,4-dihydro-2(1H)-quinolinone (1.5%) as main byproducts were obtained. On the basis of the mechanism of Friedel-Crafts alkylation, the generation mechanisms of these two compounds were proposed.

Transition metal-free functionalization of 2-oxindolesviasequential aldol and reductive aldol reactions using rongalite as a C1 reagent

“…Traditionally, 3-methylindoline-2-ones are prepared from 2-oxindoles using n -BuLi with MeI. 5 After that, many procedures have been established to accomplish 3-methyl-2-oxindoles viz ., olefin hydrocarbamoylation 6 and Friedel–Crafts alkylation, 7 but these methods each suffer from their own set of limitations such as the formation of side products, poor regioselectivity and cryogenic conditions.…”

Exploration of Oxidative Ritter-Type Reaction of α-Arylketones and Its Application for the Collective Total Syntheses of Erythrina Alkaloids

“…Starting from two commercially available building blocks 2-(3,4-dimethoxyphenyl)cyclohexan-1-one (2z) and bromoacetonitrile (3k), a key oxidative Ritter-type reaction not only installed a challenging C-5 azaquaternary carbon center but also enlarged the two-carbon chain bearing a synthetically valuable bromine atom for the subsequent ring-closing transformation under the slightly modified reaction conditions (Selectfluor 54 and PTSA were used to replace DDQ and HBF 4 , respectively; for details, please see the Supporting Information), resulting in the desired racemic amide 9. With brominated amide 9 in hand, Friedel-Crafts alkylation, 55 radical cyclization, 56 and photo-Witkop reaction 57,58 were applied to assemble a sixmembered C-ring via an intramolecular approach, respectively, and numerous reaction conditions were examined; unfortunately, no expected C-ring forming spirolactam was isolated under all conditions tried, and amide 9 was either degraded to produce a complex mixture or recovered intact. Therefore, the order of the ring-forming sequence was adjusted, and an intramolecular Reformatsky reaction was applied to first assemble the five-membered B ring.…”

The study of industrializable ionic liquid catalysts for long‐chain alkenes Friedel–Crafts alkylation

“…After 30 min, it showed no variation tendency and this demonstrated that long-chain alkene alkylation with toluene is a fast reaction. [34] Over time, the selectivity of 2-alkylate decreased slightly. This is because the catalyst has a very high catalytic efficiency, so more heat is released at the initial stage of the reaction, leading to a rise in the temperature of the reaction.…”

“…The adjustment of the electron cloud structure caused the carbocation F I G U R E 3 Effect of (a) toluene/olefin molar ratio, (b) reaction temperature, (c) catalyst dosage and (d) reaction time on the reaction rearrangement, and then the carbocation collided with toluene to form alkyl benzene. [34] The effect of temperature increase on the carbocation rearrangement reaction was prominent, so the isomerization rate increased. As a result, the temperature of the reaction was optimal at 333.15 K.…”