20717-43-5

Usage

Uses

Used in Pharmaceutical Industry:
Quinoline, decahydro-2-methylis used as an intermediate in the synthesis of various drugs and pharmaceutical compounds. Its unique chemical structure allows it to be a versatile building block for the development of new medications with potential therapeutic applications.
Used in Dye Production:
In the dye industry, Quinoline, decahydro-2-methylis used as a precursor for the production of various dyes. Its chemical properties make it suitable for creating a wide range of colors and hues, which can be used in various applications, such as textiles, paints, and plastics.
Used in Organic Synthesis:
Quinoline, decahydro-2-methylis used as a building block in organic synthesis, allowing chemists to create more complex chemical compounds with specific properties and applications. Its versatility in forming different chemical bonds and structures makes it a valuable component in the synthesis of various organic compounds.
Used in Chemical Research:
In the field of chemical research, Quinoline, decahydro-2-methylserves as a valuable compound for studying the properties and behavior of heterocyclic compounds. Its unique structure and reactivity make it an interesting subject for research, potentially leading to new discoveries and applications in various industries.

Upstream product

• 91-63-4 2-methylquinoline 
• 2617-98-3 2-methyl-5,6,7,8-tetrahydroquinoline 
• 1780-19-4 1,2,3,4-tetrahydro-2-methylquinoline 

Downstream Products

• 129-44-2 1,5-diaminoanthraquinone 
• 6937-75-3 1-amino-5-nitroanthraquinone 
• 60080-32-2 1,5-bis-hydroxyamino-anthraquinone 
• 28289-85-2 ((2S,4aR,8aR)-2-Methyl-octahydro-quinolin-1-yl)-phenyl-methanone 
• 1780-19-4 1,2,3,4-tetrahydro-2-methylquinoline 
• 91-63-4 2-methylquinoline 

Relevant academic research and scientific papers

Organometallic Synthesis of Bimetallic Cobalt-Rhodium Nanoparticles in Supported Ionic Liquid Phases (CoxRh100?x@SILP) as Catalysts for the Selective Hydrogenation of Multifunctional Aromatic Substrates

The synthesis, characterization, and catalytic properties of bimetallic cobalt-rhodium nanoparticles of defined Co:Rh ratios immobilized in an imidazolium-based supported ionic liquid phase (CoxRh100?x@SILP) are described. Following an organometallic approach, precise control of the Co:Rh ratios is accomplished. Electron microscopy and X-ray absorption spectroscopy confirm the formation of small, well-dispersed, and homogeneously alloyed zero-valent bimetallic nanoparticles in all investigated materials. Benzylideneacetone and various bicyclic heteroaromatics are used as chemical probes to investigate the hydrogenation performances of the CoxRh100?x@SILP materials. The Co:Rh ratio of the nanoparticles is found to have a critical influence on observed activity and selectivity, with clear synergistic effects arising from the combination of the noble metal and its 3d congener. In particular, the ability of CoxRh100?x@SILP catalysts to hydrogenate 6-membered aromatic rings is found to experience a remarkable sharp switch in a narrow composition range between Co25Rh75 (full ring hydrogenation) and Co30Rh70 (no ring hydrogenation).

Highly efficient one-pot multi-directional selective hydrogenation and N-alkylation catalyzed by Ru/LDH under mild conditions

Atomic economy, non-toxicity, harmlessness and multidirectional selectivity advocated by green chemistry have increasingly become a hot and difficult research topic. Herein, we present a highly efficient, one-pot tandem and easy-to-operate method through which we could directly produce a broad range of multi-directional selective hydrogenated amines or N-alkyl aliphatic amines using aromatic nitro compounds as raw materials. Ru/LDH with characteristics of layered mesoporous structure, well dispersed small Ru nanoparticles and LDH stabilization to the Ru NPs was employed as the catalyst. It is remarkable that multi-directional superb chemoselectivity to aromatic amines, alicyclic amines as well as N-alkyl aliphatic amines could be achieved with excellent catalytic activity and recyclability by tuning reaction conditions over 5wt%Ru/LDH-2. Additionally, this catalytic system also exhibited attractive activity and multi-directional chemoselectivity in the hydrogenation of quinoline and its derivatives with solvents of different polarity. Chemoselectivity to 5,6,7,8-tetrahydroquinoline derivatives could reach as high as 95.6 %.

Unique nanocages of 12CaO·7Al2O3 boost heterolytic hydrogen activation and selective hydrogenation of heteroarenes over ruthenium catalyst

The chemoselective hydrogenation of heteroarenes is one of the most important synthetic reactions for the production of key intermediates in agrochemicals, pharmaceuticals and various fine chemicals. The development of new heterogeneous catalysts for the environmentally benign synthesis of heterocycle hydrogenated products is a fundamental objective for chemists. Here, we report that 12CaO·7Al2O3 with a unique sub-nanocage structure loaded with Ru nanoparticles exhibits higher activity, chemoselectivity and sustainability for the hydrogenation of heteroarenes in a solvent-free system than traditional oxide-supported metal catalysts. Conversion of >99% and a selectivity close to 99% were achieved for the hydrogenation of quinoline under mild conditions. This catalyst was also successfully applied to the hydrogenation of a variety of N- and O-heteroarenes with high yields. The superior catalytic performance can be attributed to a cooperative effect between the hydrogen-storage ability and large amount of strong basic sites on the surface of the support, which promotes heterolytic H2 cleavage and prevents poisoning of the metal surface caused by the adsorption of heteroarenes.

Tuning the chemoselective hydrogenation of aromatic ketones, aromatic aldehydes and quinolines catalyzed by phosphine functionalized ionic liquid stabilized ruthenium nanoparticles

Ruthenium nanoparticles (Ru NPs) stabilized by phosphine-functionalized ionic liquids (PFILs) were synthesized in an imidazolium-based ionic liquid using H2 as a reductant. Characterization showed well-dispersed particles of about 2.2 nm (TEM) and confirmed the PFIL stabilization of the Ru NPs (NMR). The Ru NPs stabilized by PFILs exhibited excellent activity and switchable chemoselectivity in the heterogeneous selective hydrogenation of aromatic ketones, aromatic aldehydes and quinolines under mild conditions.

Mild hydrogenation of quinoline to decahydroquinoline over rhodium nanoparticles entrapped in aluminum oxy-hydroxide

An Rh/AlO(OH) catalyst was prepared by a sol-gel method. This catalyst showed an excellent catalytic performance for the complete hydrogenation of quinoline to decahydroquinoline at relatively mild conditions. The growth of Rh-particle size and the decrease in the number of surface hydroxyl groups during heat treatment resulted in a significant decrease in catalytic properties. The excellent catalytic performance of the fresh Rh/AlO(OH) was attributed to the cooperation between the hydroxyl groups on the support and on the active metal centers.

α-alkylation and stereochemistry of cis- and trans-decahydroquinolines mediated by the formamidine and boc activating groups. Synthesis of pumiliotoxin C 1

cis- and trans-decahydroquinolines, as their t-Boc and formamidine derivatives, have been metalated and alkylated. The former gives mainly axial alkylation whereas the latter gives equatorial alkylation in the trans series. For the cis series, the t-Boc derivative gives essentially pure equatorial alkylation as does the formamidine derivative. Several electron-transfer processes occur simultaneously with the ionic alkylation, and this can be altered by use of pentynylcopper or HMPA. Furthermore, cuprates, when employed, gave good yields of alkylation product via radical pathways, but the stereochemistry suffered. A synthesis of the poison dart frog secretion, pumiliotoxin C, has been accomplished using these alkylation techniques.

Hydrogenation Pathway of Quinolines over Raney Nickel and Ru/C

Quinoline, 2-methylquinoline, and 8-methylquinoline were hydrogenated over Raney Nickel (R-Ni) under 10 atm hydrogen pressure at about 200 deg C and over ruthenium on carbon (Ru/C) under 100 atm hydrogen pressure at 150 deg C.All the substrates were commonly hydrogenated into the initial products, 1,2,3,4-tetrahydroquinolines.The initial products were competitively converted over R-Ni to the final products, decahydroquinolines, directly or via 5,6,7,8-tetrahydroquinolines which were mainly formed from the initial products by isomerization.Ru/C promoted exclusively the direct hydrogenation of 1,2,3,4-tetrahydro derivatives to the final products.The hydrogenation and isomerization of 1,2,3,4-tetrahydroquinoline was completely inhibited in the competitive hydrogenation of quinoline and isoquinoline over R-Ni.Such features of these substrates are explained by the strong basicity of 1,2,3,4-tetrahydroisoquinoline.Roles of 1,2,3,4-tetrahydroisoquinoline are much moderate on Ru/C, where the ?-coordination may be important.The effects of methyl substituent and different reactivities of quinoline and isoquinoline are discussed in terms of the steric hindrance on adsorption, heats of hydrogenation, basicities, and electronic properties of the related compound, which are calculated according to the MNDO-PM3 method.

Regiospecific Hydrogenation of Quinolines and Indoles in the Heterocyclic Ring

Quinolines, indoles, acridine and carbazole were hydrogenated using a large variety of heterogeneous catalysts in hydrocarbon solvents in an effort to achieve selective hydrogenation of the heterocyclic ring.When quinolines were hydrogenated using supported platinum, palladium, rhodium, ruthenium, or nickel metal catalysts in the presence of hydrogen sulfide, carbon disulfide, or carbon monoxide, there was exclusive hydrogenation of the heterocyclic ring to give only 1,2,3,4-tetrahydroquinolines.Use of iridium, rhenium, molybdenum(VI) oxide, tungsten(VI) oxide, chromium(III) oxide, iron(III) oxide, cobalt(II) oxide-molybdenum(VI) oxide, or copper chromite catalysts also caused exclusive hydrogenation of the heterocyclic ring even without addition of sulfur compounds or carbon monoxide.Hydrogenation of indoles using platinum, rhenium, or, in some cases, nickel catalysts (with or without sulfur compounds) occurred exclusively in the heterocyclic ring to give indolines, but conversions were affected by indole-indoline equilibria.

N-Nitrosodecahydroquinolines. Conformational Analysis by Carbon-13 Nuclear Magnetic Resonance Spectroscopy.

NMR spectra (13C and 1H) of N-nitroso-trans-decahydroquinoline (1), N-nitroso-cis-decahydroquinoline (2), 17-methyl- or 17-tert-butyl-substituted N-nitrosodecahydroquinolines, and N-nitroso-trans-syn-trans-perhydroacridine were recor