63136-60-7

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-3-methylquinoline is utilized as an intermediate in the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs, particularly those targeting specific biological pathways or diseases.
Used in Agrochemical Industry:
In the agrochemical sector, 4-chloro-3-methylquinoline serves as an intermediate for the production of various agrochemicals. Its potential biological activities, such as antimicrobial and antifungal properties, make it a valuable compound in creating effective pesticides and fungicides.
Used in Organic Synthesis:
4-Chloro-3-methylquinoline is employed as a building block in the preparation of a wide range of heterocyclic compounds in organic synthesis. Its versatility and reactivity enable the creation of diverse organic compounds with various applications.
Used in Research and Development:
Due to its potential biological activities, 4-chloro-3-methylquinoline is also used in research and development for exploring its properties and applications in different fields. This includes studying its antimicrobial and antifungal properties for potential use in medical or environmental applications.

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

Upstream product

• 64965-46-4 3-methylquinolin-4-ol 
• 1873-55-8 3-methylquinoline N-oxide 
• 1196-28-7 2'-Aminopropiophenon 
• 68-12-2 N,N-dimethyl-formamide 
• 52457-99-5 1-(2-acetylaminophenyl)-1-propanone 
• 136613-57-5 2'-azidopropiophenone 
• 2591-86-8 N-Formylpiperidine 
• 4394-85-8 4-morpholinecarboxaldehyde 
• 62-53-3 aniline 
• 219949-95-8 ethyl 3-methyl-4-oxo-1,4‐dihydroquinoline‐2‐carboxylate 
• 858488-66-1 3-Methyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid 
• 72553-74-3 3-methylquinolin-4(1H)‐one 
• 612-58-8 3-methylquinoline 
• 858488-66-1 4-hydroxy-3-methylquinoline-2-carboxylic acid 

Downstream Products

• 1379615-61-8 4‐chloro-3-methyl‐2‐(1‐(4‐(trifluoromethoxy)benzyl)-1H‐pyrazol‐4‐yl)quinoline 
• 1379615-35-6 3-methyl-2-(1-(4‐(trifluoromethoxy)benzyl)‐1H‐pyrazol‐4-yl)quinolin‐4(1H)‐one 
• 94934-87-9 3‐methyl‐4‐phenylquinoline 

Relevant academic research and scientific papers

A novel one pot synthesis of 2-dimethylaminoquinoline derivatives from arylazido ketones by cyclization under Vilsmeier condition

1-(2-Azidophenyl)ethanone on treatment with Vilsmeier reagent yields 4- chloro-2-dimethylamino-3-quinolinecarboxaldehyde and 4-chloro-2- dimethylaminoquinoline, whereas 1-(2-azidophenyl)propanone and butanone derivatives give the corresponding 4-chloro-3-alkyl-2-dimethylaminoquinolines and 3-alkyl-4-chloroquinolines.

A novel one-pot synthesis of 2-aminoquinolines from arylazidoketones by cyclization under Vilsmeier conditions

Studies have been carried out on a new novel method for the synthesis of 2-(N,N-disubstituted)aminoquinoline via intramolecular electrophilic substitution of methyleniminium salts by azide. Treatment of 1-(2- azidophenyl)ethanone with Vilsmeier reagent (D

A new route to the synthesis of 4-chloro-3-methylquinolines from 1-(2-aminophenyl)-propanones using Vilsmeier reagent

An efficient one-step synthesis of various substituted 4-chloro-3-methylquinolines from 1-(2-aminophenyl)propanone using Vilsmeier reagent is reported.

TOLL-LIKE RECEPTOR 8 (TLR8)-SPECIFIC ANTAGONISTS AND METHODS OF MAKING AND USES THEREOF

Toll-like receptor 8 (TLR8)-specific inhibitors and methods of using the same in individuals having an autoimmune disease or an inflammatory disorder.

Potent Antimalarial 2-Pyrazolyl Quinolone bc1 (Qi) Inhibitors with Improved Drug-like Properties

A series of 2-pyrazolyl quinolones has been designed and synthesized in 5-7 steps to optimize for both in vitro antimalarial potency and various in vitro drug metabolism and pharmacokinetics (DMPK) features. The most potent compounds display no cross-resistance with multidrug resistant parasite strains (W2) compared to drug sensitive strains (3D7), with IC50 (concentration of drug required to achieve half maximal growth suppression) values in the range of 15-33 nM. Furthermore, members of the series retain moderate activity against the atovaquone-resistant parasite isolate (TM90C2B). The described 2-pyrazoyl series displays improved DMPK properties, including improved aqueous solubility compared to previously reported quinolone series and acceptable safety margin through in vitro cytotoxicity assessment. The 2-pyrazolyl quinolones are believed to bind to the ubiquinone-reducing Qi site of the parasite bc1 complex, which is supported by crystallographic studies of bovine cytochrome bc1 complex.

Structure-activity relationship of quinoline derivatives as potent and selective α2c-adrenoceptor antagonists

Starting from two acridine compounds identified in a high-throughput screening campaign (1 and 2, Table 1), a series of 4-aminoquinolines was synthesized and tested for their properties on the human α2- adrenoceptor subtypes (α2A, α2B, and α2C). A number of compounds with good antagonist potencies against the α2C-adrenoceptor and excellent subtype selectivities over the other two subtypes were discovered. For example, (R)-{4-[4-(3,4-dimethylpiperazin-1-yl)phenylamino]quinolin-3-yl}methanol 6j had an antagonist potency of 8.5 nM against, and a subtype selectivity of more than 200-fold for, the α2c-adrenoceptor. Investigation of the structure-activity relationship identified a number of structural features, the most critical of which was an absolute need for a substituent in the 3-position of the quinoline ring. The 3-position on the piperazine ring was also found to play an appreciable role, as substitutions in that position exerted a significant and stereospecific beneficial effect on the α2C- adrenoceptor affinity and potency. Replacing the piperazine ring proved difficult, with 1,4-diazepanes representing the only viable alternative.

FIBROSIS INHIBITOR

Medicament being useful as a fibrosis inhibitor for organs or tissues, which comprises a compound of the formula (I): wherein Ring Z is optionally substituted pyrrole ring, etc.; W2 is -CO-, -SO2-, optionally substituted C1-C4 alkylene, etc.; Ar2 is optionally substituted aryl, etc.; W1 and Ar1 mean the following (1) and (2):(1) W1 is optionally substituted C1-C4 alkylene, etc.; Ar1 is optionally substituted bicyclic heteroaryl having 1 to 4 nitrogen atoms as ring-forming atoms:(2) W1 is optionally substituted C2-C5 alkylene, optionally substituted C2-C5 alkenylene, etc.; and Ar1 is aryl or monocyclic heteroaryl, which is substituted by carboxyl, alkoxycarbonyl, etc. at the ortho- or meta-position thereof with respect to the binding position of W1, or a pharmaceutically acceptable salt thereof.

Pyrrole derivatives

Pyrrole derivatives represented by the following formula: wherein Ring Z is an optionally substituted pyrrole ring, etc.; W2 is —CO—, —SO2—, an optionally substituted C1-C4 alkylene, etc.; Ar2 is an optionally substituted aryl, etc.; W2 and Ar1 mean the following (1) and (2): (1) W1 is an optionally substituted C1-C4 alkylene, etc.; Ar1 is an optionally substituted bicyclic heteroaryl having 1 to 4 nitrogen atoms as ring-forming atoms: (2) W1 is an optionally substituted C2-C5 alkylene, an optionally substituted C2-C5 alkenylene, etc.; and Ar1 is an aryl or monocyclic heteroaryl, which are substituted by carboxyl, an alkoxycarbonyl, etc. at the ortho- or meta-position thereof with respect to the binding position of W1, or a pharmaceutically acceptable salt thereof These compounds are useful as medicaments such as a fibrosis inhibitor for organs or tissues.

REACTIONS OF 3-SUBSTITUTED QUINOLINE 1-OXIDES WITH ACYLATING AGENTS

Reactions of 3-fluoro- (1a), 3-bromo- (1b), 3-methyl- (1c), 3-methoxy- (1d) and 3-acetamidoquinoline 1-oxides (1e) with acylating agents (POCl3, Ac2O, TsCl and PhCOCl) were examined (Table).While only 2-substituted quinolines were obtained from 1a and 1b, fair amounts of 4-substituted products were formed in reactions of 1d, the sole formation of the 4-acetoxyquinoline (6) with Ac2O being the most significant result. 2-Chloroquinolines, 4-chloroquinolines and 2-tosyloxyquinolines were formed (and sometimes predominate) in addition to 2-quinolinones in reactions with TsCl.