92-46-6

Usage

Uses

Used in Chemical Synthesis:
6-Chloro-2-methylquinoline is used as a chemical intermediate for the synthesis of various compounds due to its unique structure and properties. Its presence of a chlorine atom and a methyl group allows for further functionalization and modification in chemical reactions.
Used in Pharmaceutical Industry:
6-Chloro-2-methylquinoline is used as a building block in the development of pharmaceutical compounds. Its unique structure can be utilized to create new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
6-Chloro-2-methylquinoline is used as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides. Its unique structure can contribute to the development of new and effective agrochemicals.
Used in Dye and Pigment Industry:
6-Chloro-2-methylquinoline is used as a starting material for the synthesis of dyes and pigments. Its unique structure can be utilized to create new dyes and pigments with specific properties.
Used in Research and Development:
6-Chloro-2-methylquinoline is used as a research compound in various scientific studies and experiments. Its unique structure and properties make it a valuable tool for understanding chemical reactions and exploring new applications.

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

Upstream product

• 732247-99-3 6-chloro-2-methyl-1,2,3,4-tetrahydro-quinolin-4-ol 
• 98-88-4 benzoyl chloride 
• 7647-01-0 hydrogenchloride 
• 7732-18-5 water 
• 64-17-5 ethanol 
• 100-00-5 4-chlorobenzonitrile 
• 15644-86-7 6-chloro-2-methyl-quinolin-4-ol 
• 28328-97-4 6-chloro-2-methyl- 1,2,3,4-tetrahydroquinoline 
• 18826-95-4 1.3-butanediol 
• 106-47-8 4-chloro-aniline 
• 109-92-2 ethyl vinyl ether 
• 74-85-1 ethene 

Downstream Products

• 104828-64-0 N,N-dimethyl-4-phenyl-2-butanamine 
• 1190876-61-9 (S)-6-chloro-2-methyl-1,2,3,4-tetrahydroquinoline 
• 1263000-44-7 (R)-6-chloro-2-methyl-1,2,3,4-tetrahydroquinoline 
• 1404093-47-5 C₁₇H₁₃ClN₂O₃ 
• 1446451-45-1 2,2'-(2-phenylpropane-1,3-diyl)bis(6-chloroquinoline) 
• 1078-28-0 6-methoxyquinaldine 
• 1608092-50-7 6-chloro-2-[(2-phenyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]quinoline 
• 860190-32-5 ethyl 6-chloroquinoline-2-carboxylate 
• 1139911-18-4 (E)-6-chloro-2-styrylquinoline 

Relevant academic research and scientific papers

Method for preparing quinoline compound through oxidation and reduction integration (by machine translation)

The method takes the aromatic nitro compound and the fatty alcohol as. the raw material and uses the aromatic nitro compound and the fatty, alcohol as the catalyst to, react under an inert atmosphere or under the, 150-200 °C atmosphere containing oxygen 2-12h, at the atmosphere, of oxygen containing, oxygen, to obtain the substituted, quinoline compound, and. the synthesis method can have important application in the aspect of quinoline compound. synthesis. (by machine translation)

Method for producing quinoline derivative through one-pot two-step method

The invention relates to a method for producing a quinoline derivative through a one-pot two-step method. According to the method, an aromatic nitro compound and fatty alcohol are used as raw materials, oxygen-containing molybdenum disulfide is used as a catalyst, firstly, under the conditions of 0.3-3.0-MPa hydrogen and 120-160 DEG C, a reaction is carried out for 2-10 h, the aromatic nitro compound is translated into an aromatic amine, then a reaction atmosphere is displaced, in an inert atmosphere or an oxygen-containing atmosphere, a reaction is carried out under the condition of 120-200 DEG C for 2-12 h, after the reaction is completed, a liquid-phase component is separated out, and is concentrated, and an obtained product is separated by a silica gel column to obtain a substituted qunoline compound. The synthesis method can have important application on the aspect of synthesis of quinoline compounds.

Deracemization of Phenyl-Substituted 2-Methyl-1,2,3,4-Tetrahydroquinolines by a Recombinant Monoamine Oxidase from Pseudomonas monteilii ZMU-T01

A monoamine oxidase (MAO5) from Pseudomonas monteilii ZMU-T01 was first heterologously expressed in Escherichia coli BL21(DE3) and then used as a biocatalyst for the deracemization of racemic 2-methyl-1,2,3,4-tetrahdroquinoline derivatives to yield the unreacted R enantiomer with up to >99 % ee. Sequence alignment revealed that MAO5 shared 14.7 % identity toward the well-studied monoamine oxidase (MAO-N).

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.

Platinum-catalyzed assembly of quinaldine from aniline and ethylene

The selectivity of the catalytic reaction between aniline and ethylene in the presence of the Brunet catalyst (PtBr2/Br-) shifts from the hydroamination product N-ethylaniline to the heterocyclization product 2-methylquinoline (quinaldine) when conducted in the presence of PPh3 (1 equiv per Pt atom). Condition optimization revealed that this process works best in the absence of any halide salt additive, that it is essentially insensitive to the nature of the halide in PtX2, that the best promoter in the PMexPh3-x series is PPh3 when used in strictly stoichiometric amounts, and that the 4-RC6H 5NH2 (R = nBu, Cl, OMe, NMe2) substrates are equally converted albeit less efficiently. Slight dilution of the system with THF or toluene slightly improves the activity, and a kinetic profile shows the presence of an induction phase and a deactivating step, which however does not involve reduction to metallic platinum contrary to the PPh3-free Brunet catalyst. Mechanistic considerations are presented.

Design, synthesis and biological evaluation of 2-substituted quinolines as potential antileishmanial agents

An analogous library of 2-substituted quinoline compounds was synthesized with the aim to identify a potential drug candidate to treat visceral leishmaniasis. These molecules were tested for their in vitro and in vivo biological activity against Leishmania donovani. Metabolic stability of these compounds was also improved through the introduction of halogen substituents. Compound (26g), found to be the most active; exhibited an IC50 value of 0.2 μM and >180 fold selectivity. The hydrochloride salt of (26g) showed 84.26 ± 4.44 percent inhibition at 50 mg/kg × 5 days (twice daily, oral route) dose in L. donovani/hamster model. The efficacy was well correlated with the PK data observed which indicating that the compound is well distributed.

One-pot photocatalytic synthesis of quinaldines from nitroarenes with Au loaded TiO2 nanoparticles

One-pot photocatalytic synthesis of quinaldines from nitroarenes using Au-TiO2 nanoparticles is reported. Au-TiO2 on irradiation induces a combined redox reaction with nitroarene and alcohol and the products undergo condensation-cyclization process to give quinaldines.

Novel redox photocatalyst Pt-TiO2 for the synthesis of 2-Methylquinolines from nitroarenes

An eco-friendly and efficient procedure for synthesis of 2-methylquinoline derivatives from nitroarenes has been developed by a simple one-pot reaction on the surface of platinum-loaded TiO2 with neat ethanol under UV irradiation without any harsh reagent according to green chemistry. TiO 2 catalysts with various amounts of Pt loadings were prepared by photodeposition using chloroplatinic acid solution and characterized by XRD, BET, AFM, HR-TEM, XPS, and DRS. XRD patterns showed that the crystal structure of Pt-TiO2 still remained as anatase phase. The UV-vis spectra indicated that Pt promoted the absorption of visible light. The XPS measurements reveal that platinum particles are present mainly in metallic form. AFM and HR-TEM analysis revealed the presence of nonspherical shaped platinum nanoparticles of the diameter 312 nm. Pt-TiO2 on irradiation induces a combined redox reaction with nitroarene and alcohol and this is followed by condensationcyclization of aniline and oxidation products to give 2-methylquinolines

Assembly of substituted 2-alkylquinolines by a sequential palladium-catalyzed Ci-N and Ci-C bond formation

Diversity: A range of substituted 2-alkylquinolines can be prepared in a general and efficient synthetic approach that employs mild reaction conditions (see scheme). The synthesis is based on a sequential palladium-catalyzed Ci-N and Ci-C bond formation, followed by palladium-catalyzed aromatization, and results in the formation of the desired compounds in one step. Copyright

CAN-catalyzed three-component reaction between anilines and alkyl vinyl ethers: stereoselective synthesis of 2-methyl-1,2,3,4-tetrahydroquinolines and studies on their aromatization

The CAN-catalyzed reaction between anilines and vinyl ethers at room temperature provides a convenient and efficient access to?4-alkoxy-2-methyl-1,2,3,4-tetrahydroquinolines. This reaction is stereoselective, favouring a cis arrangement for the alkoxy and methyl groups, and involves a three-component process that leaves a molecule of alcohol as the only side product. 2-Methylquinoline derivatives were efficiently prepared from 4-alkoxy-2-methyl-1,2,3,4-tetrahydroquinolines by Pd-C-promoted dehydrogenation.