4964-69-6

Usage

Uses

Used in Agrochemical Industry:
5-Chloroquinaldine is used as an intermediate in the synthesis of various agrochemicals for crop protection. It is used as a building block for the production of pesticides and herbicides, contributing to the development of effective and efficient crop protection products.
Used in Pharmaceutical Industry:
5-Chloroquinaldine is utilized in the manufacturing of pharmaceuticals, serving as a key component in the synthesis of various drugs. Its role as an intermediate allows for the development of new and innovative pharmaceuticals to address various health conditions.
Used in Research Chemicals:
5-Chloroquinaldine is employed in the production of research chemicals, providing a foundation for scientific investigations and advancements in various fields. Its use in research facilitates the discovery of new compounds and their potential applications.

InChI:InChI=1/C10H8ClN/c1-7-5-6-8-9(11)3-2-4-10(8)12-7/h2-6H,1H3

Upstream product

• 75-07-0 acetaldehyde 
• 108-42-9 3-chloro-aniline 
• 50-00-0 formaldehyd 
• 123-73-9 trans-Crotonaldehyde 
• 18826-95-4 1.3-butanediol 
• 107-21-1 ethylene glycol 
• 4784-77-4 (E)-1-Bromo-2-butene 
• 15426-14-9 3,3'-dichloroazobenzene 
• 64-17-5 ethanol 
• 106237-28-9 β-(m-chloroanilino)crotonaldehyde 

Downstream Products

• 1365920-50-8 C₂₃H₂₀N₂S 
• 511231-70-2 5-chloro-quinoline-2-carboxylic acid 
• 63010-74-2 4,5-dichloro-2-methyl-quinoline 
• 143840-93-1 sodium {3-[2-(5-chloro-2-quinolinyl)-(E)-ethenyl]phenoxy}butanoate 
• 108165-12-4 4-{3-[(E)-2-(5-Chloro-quinolin-2-yl)-vinyl]-phenoxy}-butyric acid ethyl ester 
• 1027848-32-3 3-[(E)-2-(5-Chloro-quinolin-2-yl)-vinyl]-phenol 
• 1027374-02-2 Acetic acid 3-[(E)-2-(5-chloro-quinolin-2-yl)-vinyl]-phenyl ester 

Relevant academic research and scientific papers

Quinolines synthesis by reacting 1,3-butanediol with anilines in the presence of iron catalysts

2-, 4-, 6-, 7-, and 8-substituted quinolines were synthesized in 78–95% yield by the reaction of 1,3- butanediol with anilines in the presence of iron catalysts in carbon tetrachloride.

Quinoline Synthesis by the Reaction of Anilines with 1,2-diols Catalyzed by Iron Compounds

The synthesis of quinoline derivatives by cyclocondensation of anilines with 1,2-ethanediol, 1,2-propanediol, and 1,2-butanediol in the presence of iron-containing catalysts was performed for the first time.

Copper-Promoted Tandem Reaction of Azobenzenes with Allyl Bromides via N=N Bond Cleavage for the Regioselective Synthesis of Quinolines

A copper-promoted tandem reaction of a variety of azobenzenes and allyl bromides via N=N bond cleavage to regioselectively construct quinoline derivatives has been developed. The azobenzenes act as not only construction units but also an oxidant for quinoline formation.

Synthesis of substituted quinolines by the reaction of anilines with alcohols and CCl4 in the presence of Fe-containing catalysts

Substituted quinolines were synthesized by the reaction of aniline derivatives with aliphatic alcohols and CCl4 upon the action of the FeCl3·6H2O catalyst.

Preparation and Cyclodehydration of β-Arylaminocrotonaldehyde

β-Arylaminocrotonaldehydes (3) were prepared by alkaline hydrolysis of 1-arylamino-3-arylimino-1-butenes (2).On treatment with sulfuric acid, β-anilinocrotonaldehyde (3b) and p-methyl- (3a), m-chloro- (3c), and p-chloro- (3d) derivatives were cyclodehydrated to give the corresponding quinaldines in quantitative yields.The protonation of 3 was proved to take place at the oxygen atom on the basis of spectral evidence.The mechanism of the cyclodehydration is discussed.Keywords-Combes reaction; cyclodehydration; hydrolysis; β-arylaminocrotonaldehyde; 1-arylamino-3-arylimino-1-butene; quinaldine derivative; protonation

A Kinetic Study of Cyclodehydration of β-Arylaminocrotonaldehyde Derivatives

Cyclodehydration of β-arylaminocrotonaldehydes (1) was studied kinetically in comparison with those of β-(p-toluidino)acrolein (2a) and 4-(p-toluidino)-3-penten-2-one (3a).The rate constants k1 of cyclodehydration of 1 were not consistent with the Zucker-Hammett hypothesis, i.e., log k1 was related linearly to -H0, but the slopes were between 1.28 and 1.36.Bunnett-Olsen plots for log k1 were linear.Statistically corrected values of log k0r/KSH(+) were applied to Jaffe's four-parameter Hammett equation.The reaction constant for the site of the aromatic ring at which cyclodehydration takes place was evaluated to be -8.54, and that for the oxobutenylamino group was evaluated to be +0.72.The effect of substituents on the aromatic ring upon the reactivity is discussed.Keywords - kinetic study; cyclodehydration; Combes reaction; β-arylaminocrotonaldehyde; quinaldine derivative; Zucker-Hammett hypothesis; Bunnett-Olsen plot; four-parameter Hammett equation

The Rhodium Complex-catalyzed Synthesis of Quinolines from Aminoarenes and Aliphatic Aldehydes

A variety of aminoarenes react with aliphatic aldehydes in the presence of a catalytic amount of a rhodium complex and an excess amount of the corresponding nitroarenes at 180 deg C to give 2-alkyl- and 2,3-dialkyl-substituted quinolines in excellent yields.Among the rhodium complexes examined, 2 exhibits the highest activity as a catalyst.Thus, 2-methyl-, 2-ethyl-3-methyl-, 2-propyl-3-ethyl-, 2-butyl-3-propylquinoline derivatives are readily obtained from aminoarenes and ethanal, propanal, butanal, and pentanal respectively.