3299-46-5

Usage

Structure

A quinoline derivative with a chlorine atom at the 6th position, an ethyl group at the 3rd position, and a propyl group at the 2nd position

Common uses

Building block in the synthesis of pharmaceuticals and agrochemicals

Applications

Development of antimalarial, antifungal, and antibacterial medications

Additional uses

Reagent in organic synthesis, intermediate in the production of various chemical products

InChI:InChI=1/C14H16ClN/c1-3-5-13-10(4-2)8-11-9-12(15)6-7-14(11)16-13/h6-9H,3-5H2,1-2H3

Upstream product

• 123-72-8 butyraldehyde 
• 100-00-5 4-chlorobenzonitrile 
• 102-82-9 tributyl-amine 
• 106-47-8 4-chloro-aniline 

Relevant academic research and scientific papers

Synthesis of quinoline derivatives from anilines and aldehydes catalyzed by Cp2ZrCl2 and recyclable Cp2ZrCl2/MCM-41 system

A facile method for the synthesis of quinoline derivatives using catalytic amount of Cp2ZrCl2 or Cp2ZrCl2 supported on MCM-41 (Cp2ZrCl2/MCM-41) in reaction of anilines and aldehydes is described. When Cp2ZrCl2/MCM-41 was used as catalyst, the yields of quinolines were enhanced by 5-15% compared with Cp2ZrCl2 as catalyst alone under the same reaction conditions. More importantly, Cp2ZrCl2/MCM-41 catalyst can be reused at least thrice by simple recover via filtration in air. Moreover, both Cp2ZrCl2 and Cp2ZrCl2/MCM-41 showed good catalytic activities to generate corresponding quinoline derivatives in moderate to good yields by varying the substituent of aniline and aldehyde. And the reaction conditions were optimized by studying the influences of reactant ratio, additives, solvent effect and reaction temperatures.

Ruthenium-catalyzed reductive cyclization of nitroarenes with trialkylamines leading to quinolines

Nitroarenes react with trialkylamines in the presence of a catalytic amount of a ruthenium catalyst together with tin(H) chloride dihydrate at 180 °C in an aqueous medium (toluene-H2O) to afford the corresponding quinoles in moderate to good yields. The catalytic pathways seems to be proceeded via a sequence involving initial reduction of nitroarenes to anilines, alkyl group transfer from alkylamines to anilines to form an imine, dimerization of imine, and heterocyclization.

Synthesis of quinolines via ruthenium-catalysed amine exchange reaction between anilines and trialkylamines

Anilines react with an array of trialkylamines in the presence of a catalytic amount of RuCl3*nH2O and bis(diphenylphosphino)methane together with SnCl2*2H2O and hex-1-ene as hydrogen acceptor in dioxane at 180 deg C to afford the corresponding 2,3-disubstituted quinolines in moderate to good yields.

The Transition Metal-catalyzed N-Alkylation and N-heterocyclization. A Reductive Transformation of Nitroarenes into (Dialkylamino)arenes and 2,3-Dialkyl-substituted Quinolines Using Aliphatic Aldehydes under Carbon Monoxide

The catalytic N-alkylation and N-heterocyclization of nitroarenes occur at 180 deg C under a carbon monoxide pressure of 70 atm and in the presence of aldehyde and such transitionmetal complexes as rhodium and palladium complexes, thus giving 2,3-dialkyl-substituted quinolines and (dialkylamino)arenes in good yields.The product selectivity depends greatly on the catalysts: a binary catalyst, RhCl(PPh3)3 and PdCl2, is effective for the N-heterocyclization, while is effective for the N-alkylation.