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Usage

Uses

Used in Chemical Synthesis:
3-Methylquinoline is used as a key intermediate in the synthesis of dyes, food coloring agents, and pharmaceutical reagents. Its chemical properties make it a suitable candidate for these applications, allowing for the creation of a wide range of products with diverse colors and functionalities.
Used in Environmental Applications:
It can be degraded efficiently by QL-degrading bacteria, which highlights its potential use in environmental applications for biodegradation and waste management.
Used in Research and Development:
3-Methylquinoline may be used as a carbon, nitrogen, and energy supplement to investigate its degradation by Comamonas testosteroni 63, providing valuable insights into the bacterial degradation process and its potential applications in bioremediation.
Used in Coordination Chemistry:
3-Methylquinoline is used as a ligand in the preparation of tetra-μ-benzoato-bis[(3-methylquinoline)copper(II)], a paddle-wheel-type dinuclear complex. This application showcases its utility in coordination chemistry and the development of novel metal complexes with potential applications in various fields.

Synthesis Reference(s)

Tetrahedron Letters, 32, p. 569, 1991 DOI: 10.1016/S0040-4039(00)74829-5

InChI:InChI=1/C10H9N/c1-8-6-9-4-2-3-5-10(9)11-7-8/h2-7H,1H3

Upstream product

• 75-21-8 oxirane 
• 62-53-3 aniline 
• 50-00-0 formaldehyd 
• 123-38-6 propionaldehyde 
• 109-87-5 Dimethoxymethane 
• 98-47-5 3-Nitrobenzenesulfonic acid 
• 57876-69-4 2-chloro-3-methyl-quinoline 
• 73177-27-2 2-ethyl-1,4-dihydro-2H-benz[d][1,3]oxazine 
• 201230-82-2 carbon monoxide 
• 32704-22-6 2-allyl-phenylamine 
• 131470-23-0 1-(2'-aminophenyl)prop-2-en-1-ol 
• 56149-65-6 3-methyl-1,5-diphenyl-1,5-diazapentadiene 
• 22892-88-2 1,4-dimethyl-5-phenyl-2-aza-1-oxapentadiene 
• 615-43-0 2-iodophenylamine 

Downstream Products

• 3222-49-9 5-methylnicotinic acid 
• 13669-42-6 3-quinolylcarboxaldehyde 
• 1873-55-8 3-methylquinoline N-oxide 
• 28712-62-1 3-methyl-5,6,7,8-tetrahydroquinoline 
• 20668-20-6 3-methyl-1,2,3,4-tetrahydroquinoline 
• 6480-68-8 quinoline-3-carboxylic acid 
• 103754-53-6 3-methyl-5-nitroquinoline 
• 2801-32-3 3-methyl-8-nitroquinoline 
• 74212-52-5 1-phenyl-2-(quinolin-3-yl)ethan-1-one 
• 57443-82-0 1,1-diphenyl-2-(3-quinolyl)ethanol 
• 139962-74-6 2-Phenyl<1H>pyrrolo<2,3-b>quinoline 
• 139962-75-7 2-(4-Methoxyphenyl)<1H>pyrrolo<2,3-b>quinoline 
• 53636-65-0 5-methyl-pyridine-2,3-dicarboxylic acid 
• 153886-69-2 3-methyl-8-quinolinesulfonic acid 

Relevant academic research and scientific papers

Potent mutagenic potential of 4-methylquinoline: Metabolic and mechanistic considerations

4-Methylquinoline (4-MeQ) showed an extraordinarily potent mutagenicity when compared to quinolone and isomeric methylquinolines. The major metabolite of 4-MeQ was 4- hydroxymethylquinoline, which was not mutagenic under the assay condition employed. Deuteration of the methyl group of 4-MeQ resulted in a decrease in the amount of the hydroxymethyl metabolic and an increase in mutagenicity, indicating that hydroxylation of the substituent methyl group is a detoxication process. A 3-chloro derivative of 4-MeQ was proven to be non-mutagenic. 4-Ethyl- quinoline, as well as 4-hydroxymethylquinoline, was much less mutagenic than 4-MeQ. Taking account of the structure-mutagenicity relationship, a possible mechanism is proposed for the potent mutagenic potential of 4-MeQ.

Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations

Photoactive two-dimensional covalent organic frameworks (2D-COFs) have become promising heterogenous photocatalysts in visible-light-driven organic transformations. Herein, a visible-light-driven selective aerobic oxidation of various small organic molecules by using 2D-COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone-based 2D-COF-1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2-chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale-up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D-COF-1 in photocatalytic cycle.

Highly Ordered Mesoporous Cobalt Oxide as Heterogeneous Catalyst for Aerobic Oxidative Aromatization of N-Heterocycles

N-heterocycles are key structures for many pharmaceutical intermediates. The synthesis of such units normally is conducted under homogeneous catalytic conditions. Among all methods, aerobic oxidative aromatization is one of the most effective. However, in homogeneous conditions, catalysts are difficult to be recycled. Herein, we report a heterogeneous catalytic strategy with a mesoporous cobalt oxide as catalyst. The developed protocol shows a broad applicability for the synthesis of N-heterocycles (32 examples, up to 99 % yield), and the catalyst presents high turnover numbers (7.41) in the absence of any additives. Such a heterogenous approach can be easily scaled up. Furthermore, the catalyst can be recycled by simply filtration and be reused for at least six times without obvious deactivation. Comparative studies reveal that the high surface area of mesoporous cobalt oxide plays an important role on the catalytic reactivity. The outstanding recycling capacity makes the catalyst industrially practical and sustainable for the synthesis of diverse N-heterocycles.

Iron(II)-Catalyzed Aerobic Biomimetic Oxidation of N-Heterocycles

Herein, an iron(II)-catalyzed biomimetic oxidation of N-heterocycles under aerobic conditions is described. The dehydrogenation process, involving several electron-transfer steps, is inspired by oxidations occurring in the respiratory chain. An environmentally friendly and inexpensive iron catalyst together with a hydroquinone/cobalt Schiff base hybrid catalyst as electron-transfer mediator were used for the substrate-selective dehydrogenation reaction of various N-heterocycles. The method shows a broad substrate scope and delivers important heterocycles in good-to-excellent yields.

Method for realizing oxidative dehydrogenation of nitrogen-containing heterocyclic ring by using biomass-based carbon material

The invention provides a method for realizing oxidative dehydrogenation of a nitrogen-containing heterocyclic ring by using a biomass-based carbon material, and belongs to the field of organic synthesis. According to the method, the raw materials of the biomass-based carbon material comprise wheat, sorghum, rice, corn straw, wheat straw, peanut shells, sesame shells, bean shells and the like, and are crushed and then ground into powder, the powder is fully mixed with an inorganic alkali, and calcination is performed in an inert gas atmosphere to prepare the biomass-based carbon material; and by using air as an oxygen source, at a temperature of 50-120 DEG C, oxidative dehydrogenation of nitrogen-containing heterocyclic compounds to synthesize quinoline compounds, isoquinoline compounds, acridine compounds, quinazoline compounds, indole compounds, imine compounds, and even quinoline compounds with pharmaceutical activity can be achieved. According to the present invention, easily available wheat flour is adopted as a raw material to prepare a non-metal catalyst, the alkali is not added during the reaction process, and a remarkable industrial application prospect is achieved.

Highly Chemoselective Deoxygenation of N-Heterocyclic N-Oxides Using Hantzsch Esters as Mild Reducing Agents

Herein, we disclose a highly chemoselective room-temperature deoxygenation method applicable to various functionalized N-heterocyclic N-oxides via visible light-mediated metallaphotoredox catalysis using Hantzsch esters as the sole stoichiometric reductant. Despite the feasibility of catalyst-free conditions, most of these deoxygenations can be completed within a few minutes using only a tiny amount of a catalyst. This technology also allows for multigram-scale reactions even with an extremely low catalyst loading of 0.01 mol %. The scope of this scalable and operationally convenient protocol encompasses a wide range of functional groups, such as amides, carbamates, esters, ketones, nitrile groups, nitro groups, and halogens, which provide access to the corresponding deoxygenated N-heterocycles in good to excellent yields (an average of an 86.8% yield for a total of 45 examples).

Catalytic Aerobic Dehydrogenatin of N-Heterocycles by N-Hydoxyphthalimide

Catalytic methods for the aerobic dehydrogenation of N-heterocycles are reported. In most cases, indoles are accessed efficiently from indolines using catalytic N-hydroxyphthalimide (NHPI) as the sole additive under air. Further studies revealed an improved catalytic system of NHPI and copper for the preparation of other heteroaromatics, for example quinolines. (Figure presented.).

Method for preparation of quinoline compounds

The invention discloses a green preparation method of quinoline compounds. According to the method, cheap and easily available copper salt and N-hydroxyphthalimide are used as catalysts, oxygen is used as an oxidizing agent, oxidation of tetrahydroquinoline compounds is performed in an organic solvent, and synthesis of quinoline compounds is realized. The method has the advantages of simple reaction operation, low reaction cost, high yield, low metal pollution and the like.

Visible-Light-Promoted Efficient Aerobic Dehydrogenation of N-Heterocycles by a Tiny Organic Semiconductor Under Ambient Conditions

An efficient reusable catalytic system has been developed based on perylene diimide (PDI) organic semiconductor for the aerobic dehydrogenation of N-heterocycles with visible light. This practical catalytic system without any additives proceeds under ambient conditions. The minute aggregates of PDI molecules on the surface of SiO2 nanospheres form tiny organic semiconductors, resulting in high-efficiency photo-oxidative activity. Notably, the robustness of this method is demonstrated by the synthesis of a wide range of N-heteroarenes, gram-scale experiments as well as reusability tests.

Iodine-catalyzed convergent aerobic dehydro-aromatization toward benzazoles and benzazines

An iodine-catalyzed aerobic dehydro-aromatization has been developed, providing straightforward and efficient access to various benzoazoles and benzoazines. The present transition-metal-free protocol enables the dehydro-aromatization of tetrahydrobenzazoles and tetrahydroquinolines with molecular oxygen as the green oxidant, along with some other N-heterocycles. Hence, a broad range of heteroaromatic compounds are generated in moderate to good yields under facile reaction conditions.