91-61-2

Usage

Uses

Used in Pharmaceutical Industry:
6-METHYL-1,2,3,4-TETRAHYDROQUINOLINE is used as a pharmaceutical intermediate for the synthesis of various drugs. Its unique chemical properties make it a valuable component in the development of new medications, contributing to the advancement of healthcare and treatment options.

InChI:InChI=1/C10H13N/c1-8-4-5-10-9(7-8)3-2-6-11-10/h4-5,7,11H,2-3,6H2,1H3

Upstream product

• 91-62-3 6-methylquinoline 
• 34847-16-0 6-methyl-3,4-dihydroquinoline-1(2H)-carbaldehyde 
• 1125-81-1 2-methyl-1,2-dihydroquinoline 
• 50624-35-6 1,4-dihydroquinoline 
• 97531-28-7 6-methyl-1,2-dihydroquinoline 
• 60375-56-6 (E)-3-amino-3-phenylacrylonitrile 
• 7647-01-0 hydrogenchloride 
• 64-19-7 acetic acid 
• 106-49-0 p-toluidine 
• 15258-46-5 N-allyl-p-toluidine 
• 4053-42-3 6-methylquinoline-N-oxide 
• 23395-72-4 quinoline-6-carbonitrile 
• 34897-84-2 2-amino-5-methylbenzyl alcohol 
• 64-17-5 ethanol 

Downstream Products

• 91-62-3 6-methylquinoline 
• 93817-07-3 1-benzoyl-6-methyl-1,2,3,4-tetrahydro-quinoline 
• 129247-22-9 N-(6-Methyl-3,4-dihydro-2H-quinolin-1-yl)-2-phenyl-acetamide 
• 104828-68-4 N,N-dimethyl-3-(3'-tolyl)propylamine 
• 103661-41-2 C₁₁H₁₂ClNO 
• 1224638-85-0 [2-(3-chloro-4-fluoro-phenoxy)-pyridin-3-yl]-(6-methyl-3,4-dihydro-2H-quinolin-1-yl)-methanone 
• 1224638-39-4 [2-(2,5-dichloro-phenoxy)-pyridin-3-yl]-(6-methyl-3,4-dihydro-2H-quinolin-1-yl)-methanone 
• 905196-07-8 C₁₇H₁₉NO₂S 
• 928743-69-5 1-tosyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid (2,4,6-mesityl)amide 
• 1163239-60-8 C₁₇H₁₇NO₄S 
• 887749-24-8 8-bromo-6-methyl-1,2,3,4-tetrahydroquinoline 

Relevant academic research and scientific papers

Heterogeneous Hydrogenation of Quinoline Derivatives Effected by a Granular Cobalt Catalyst

We communicate a convenient method for the pressure hydrogenation of quinolines in aqueous solution by using a particulate cobalt-based catalyst that is prepared in situ from simple Co(OAc)2 4H2O through reduction with abundant zinc powder. This catalytic protocol permits a brisk and atom-efficient access to a variety of 1,2,3,4-tetrahydroquinolines thereby relying solely on easy-to-handle reagents that are all readily obtained from commercial sources. Both the reaction setup assembly and the autoclave charging procedure are conducted on the bench outside an inert-gas-operated containment system, thus rendering the overall synthesis time-saving and operationally very simple.

Homogeneous pressure hydrogenation of quinolines effected by a bench-stable tungsten-based pre-catalyst

We report on an operationally simple catalytic method for the tungsten-catalyzed hydrogenation of quinolines through the use of the easily handled and self-contained precursor [WCl(η5-Cp)(CO)3]. This half sandwich complex is indefinitely storable on the bench in simple screw-capped bottles or stoppered flasks and can, if required, be prepared on a multi-gram scale while the actual catalytic transformations were performed in the presence of a Lewis acid in order to achieve both decent substrate conversions and product yields. The described method represents a facile and atom-efficient access to a variety of 1,2,3,4-tetrahydroquinolines that circumvents the use of cost-intensive and oxygen-sensitive phosphine ligands as well as auxiliary hydride reagents.

Method for preparing tetrahydroquinoline compounds by catalytic hydrogenation of ruthenium catalyst

The invention relates to a method for preparing tetrahydroquinoline compounds by catalytic hydrogenation of a ruthenium catalyst, which comprises the following steps: by using p-cymene ruthenium chloride dimer as a catalyst and hydrogen as a reducing agent, mixing the p-cymene ruthenium chloride dimer, phosphine ligand and quinoline compounds, and dissolving the mixture in an organic solvent to react, and carrying out post-treatment to obtain the tetrahydroquinoline derivative. Compared with the prior art, the method has the advantages of easily available raw materials, mild conditions, simpleoperation, atom economy, simple and green synthesis process, mild reaction conditions, excellent selectivity, high yield and good reaction universality, and has a wide application value in fine chemical intermediate synthesis.

Utilization of renewable formic acid from lignocellulosic biomass for the selective hydrogenation and/or N-methylation

Lignocellulosic biomass is one of the most abundant renewable sources in nature. Herein, we have developed the utilization of renewable formic acid from lignocellulosic biomass as a hydrogen source and a carbon source for the selective hydrogenation and further N-methylation of various quinolines and the derivatives, various indoles under mild conditions in high efficiencies. N-methylation of various anilines is also developed. Mechanistic studies indicate that the hydrogenation occurs via a transfer hydrogenation pathway.

Water-involving transfer hydrogenation and dehydrogenation of N-heterocycles over a bifunctional MoNi4 electrode

A room-temperature electrochemical strategy for hydrogenation (deuteration) and reverse dehydrogenation of N-heterocycles over a bifunctional MoNi4 electrode is developed, which includes the hydrogenation of quinoxaline using H2O as the hydrogen source with 80% Faradaic efficiency and the reverse dehydrogenation of hydrogen-rich 1,2,3,4-tetrahydroquinoxaline with up to 99% yield and selectivity. The in situ generated active hydrogen atom (H*) is plausibly involved in the hydrogenation of quinoxaline, where a consecutive hydrogen radical coupled electron transfer pathway is proposed. Notably, the MoNi4 alloy exhibits efficient quinoxaline hydrogenation at an overpotential of only 50 mV, owing to its superior water dissociation ability to provide H* in alkaline media. In situ Raman tests indicate that the NiII/NiIII redox couple can promote the dehydrogenation process, representing a promising anodic alternative to low-value oxygen evolution. Impressively, electrocatalytic deuteration is easily achieved with up to 99% deuteration ratios using D2O. This method is capable of producing a series of functionalized hydrogenated and deuterated quinoxalines.

Nano-Ni-MOFs: High Active Catalysts on the Cascade Hydrogenation of Quinolines

Abstract: The reduction of nitrogen-containing heterocyclic compounds in aqueous medium under mild condition is quite challenging. In view of metal–organic frameworks (MOFs) possess adjustable pore size and modifiable organic linkers, MOFs could be used in heterogeneous catalysis. Herein, Three Nano-Ni-MOFs, MOF-74-Ni, MOF-69-Ni, and Ni–NH2 (constructed from similar ligands and Ni2+ ions) are introduced for hydrogenating of azacyclo-compounds. As expected, Ni–NH2 shows outstanding activity of hydrogenation of quinoline under mild conditions, due to the moderate pore size and the modified –NH2 function group, which makes the substrate anchored on the surface of the framework facilitate the following catalysis process. Theoretical calculations identified that the –NH2 group at the catalyst facilitates the H2 heterolytic dissociation for the hydrogenation reactions. Graphic Abstract: Compared to MOF-74-Ni and MOF-69-Ni, the catalyst of Ni–NH2 shows outstanding activity of hydrogenation of quinoline, due to the modified –NH2 function group which makes the substrate anchored on the surface of the framework facilitate the following catalysis process[Figure not available: see fulltext.]

Geometric and electronic effects on the performance of a bifunctional Ru2P catalyst in the hydrogenation and acceptorless dehydrogenation of N-heteroarenes

The development of bifunctional catalysts for the efficient hydrogenation and acceptorless dehydrogenation of N-heterocycles is a challenge. In this study, Ru2P/AC effectively promoted reversible transformations between unsaturated and saturated N-heterocycles affording yields of 98% and 99%, respectively. Moreover, a remarkable enhancement in the reusability of Ru2P/AC was observed compared with other Ru-based catalysts. According to density functional theory calculations, the superior performance of Ru2P/AC was ascribed to specific synergistic factors, namely geometric and electronic effects induced by P. P greatly reduced the large Ru-Ru ensembles and finely modified the electronic structures, leading to a low reaction barrier and high desorption ability of the catalyst, further boosting the hydrogenation and acceptorless dehydrogenation processes.

Encapsulating Cobalt into N-Doping Hollow Frameworks for Efficient Cascade Catalysis

The development of nonprecious catalysts for hydrogenation of organic molecules is of great importance in heterogeneous catalysis. Herein, we report a series of N-doped hollow carbon frameworks encompassing cobalt nanoparticles (denoted as Co@NHF-900) constructed as a new kind of reusable catalyst for this purpose by pyrolysis of ZIF-8@Co-dopamine under Ar atmospheres. Notably, the framework of ZIF-8 is essential for efficient catalyst by providing a carbon framework to support Co-dopamine. The experimental results reveal that the ZIF-8 renders a large hollow place within the catalysts, allowing the enrichment of the substrate and windows of the hollow structure and the ease of mass transfer of products during the reaction. All of the virtues made Co@NHF-900 a good candidate for hydrogenation of quinolines with high activity (TOF value of 119 h-1, which is several times than that of akin catalysts) and chemoselectivity.

Cu-Catalyzed Chemoselective Reduction of N-Heteroaromatics with NH3·BH3 in Aqueous Solution

An efficient catalytic system was successfully developed on reduction of N-heteroaromatics with H3N?BH3 as hydrogen source in CuSO4 solution, featuring excellent chemoselectivity as well as very broad functional group tolerance. Various challenging substrates, such as OH-, NH2-, Cl-, Br-, etc., contained quinolines, quinoxalines, 1,5-naphthyridines and quinazolines were all reduced smoothly. Mechanistic studies suggested that [Cu-H] intermediate might be generated from NH3?BH3, which was believed to form with H3N?BH3 in CuSO4 solution.

Cu Nanoclusters Anchored on the Metal-Organic Framework for the Hydrolysis of Ammonia Borane and the Reduction of Quinolines

Free-access active sites created and the interaction regulated between them and substrates during the heterogeneous catalysis process are crucial, which remain a great challenge. In this work, in suit reduced to afford naked Cu nanoparticles (NPs) have been anchored on the metal-organic framework (MOF), NH2-MOF, to form Cu-NH2-MOF. The strategy can precisely control the Cu NP formation with small size and uniform distribution. The Cu NP properties and MOF advantages have been integrated to create a great catalyst with multiple functions and have resulted in improving the recyclability and superb catalytic activity for the one-pot reduction of heterocycle reactions under mild conditions. The experimental and theoretical calculation results show that the superior performance should be attributed to the framework of NH2-MOF that provides large caves for substrate enrichment and the stabilization of Cu sites by the -NH2 group.