91-62-3

Usage

Uses

Used in Pharmaceutical Synthesis:
6-Methylquinoline serves as a building block for the synthesis of various pharmaceutical compounds and biologically active substances. It is particularly utilized in the preparation of pyranobenzopyrone compounds, which exhibit anti-norovirus activity.
Used in Biological Research:
In the field of microbiology, 6-Methylquinoline acts as a primary carbon source in the culture of Pseudomonas putida QP1, aiding in the study and understanding of bacterial metabolism and growth.
Used in Analytical Chemistry:
6-Methylquinoline finds application in the synthesis of fluorescent halide-sensitive quinolinium dyes and fluorescent probes. These are employed for the determination of chloride in biological systems, providing a valuable tool for researchers in the field of analytical chemistry.
Used in Beverage Industry:
6-Methylquinoline has been reported to be found in Finnish and Japanese whiskey, contributing to the unique flavor profiles and aromatic characteristics of these spirits.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

6-Methylquinoline is sensitive to prolonged exposure to light. May react vigorously with strong oxidizing agents and strong acids . Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Fire Hazard

6-Methylquinoline is probably combustible.

Biochem/physiol Actions

6-Methylquinoline undergoes biodegradation by quinoline-degrading culture of Pseudomonas putida.

Synthesis

6-Methylquinoline is obtain from coal tar, by synthesis from p-aminobenzaldehyde and acetone.

Purification Methods

Reflux it with BaO, then fractionally distil it. Further purified it via its recrystallised ZnCl2 complex (m 190o). [Cumper et al. J Chem Soc 1176 1962, Beilstein 20 III/IV 3498, 20/7 V 400.]

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

Upstream product

• 91-61-2 6-methyl-1,2,3,4 tetrahydroquinoline 
• 1600-27-7 mercury(II) diacetate 
• 106-49-0 p-toluidine 
• 56-81-5 glycerol 
• 99-99-0 1-methyl-4-nitrobenzene 
• 501-60-0 1,2-di(p-tolyl)diazene 
• 52601-68-0 (+/-)-6t-methyl-(4ar,8at)-decahydro-quinoline 
• 50624-35-6 1,4-dihydroquinoline 
• 97531-28-7 6-methyl-1,2-dihydroquinoline 
• 579-10-2 N-acetyl-N-methylaniline 
• 4485-91-0 1-(p-methoxyphenylamino)-3-(p-methylphenylimino)-1-propene 
• 14618-59-8 N-(tert-butoxycarbonyl)-4-methylaniline 
• 1611-78-5 1,3-bis-dimethylaminotrimethinium perchlorate 
• 66763-08-4 3-(p-toluidino)-1-oxo-2-propene-2-sulfonic acid 

Downstream Products

• 34847-16-0 6-methyl-3,4-dihydroquinoline-1(2H)-carbaldehyde 
• 50971-15-8 2-(4-chloro-phenyl)-6-methyl-quinoline 
• 199168-51-9 (2-(4-methoxyphenyl)-6-methylquinoline) 
• 84614-80-2 1-benzyl-6-methyl-quinolinium; chloride 
• 53425-61-9 1-benzoyl-6-methyl-1,2-dihydro-quinoline-2-carbonitrile 
• 30479-21-1 dimethyl[4-(6-methylquinolin-2-yl)phenyl]amine 
• 89836-49-7 3-benzyl-6-methyquinoline 
• 108975-91-3 3-benzyl-6-methyl-1,2,3,4-tetrahydro-quinoline 
• 14061-24-6 6-methyl-(N-methyl-quinolinium iodide) 
• 4113-04-6 quinoline-6-carbaldehyde 
• 20150-84-9 2-amino-6-methylquinoline 
• 4053-34-3 6-Methyl-2-hydroxyquinoline 
• 4053-42-3 6-methylquinoline-N-oxide 
• 91-61-2 6-methyl-1,2,3,4 tetrahydroquinoline 

Relevant academic research and scientific papers

Metal-Free Deoxygenation of Amine N-Oxides: Synthetic and Mechanistic Studies

We report herein an unprecedented combination of light and P(III)/P(V) redox cycling for the efficient deoxygenation of aromatic amine N-oxides. Moreover, we discovered that a large variety of aliphatic amine N-oxides can easily be deoxygenated by using only phenylsilane. These practically simple approaches proceed well under metal-free conditions, tolerate many functionalities and are highly chemoselective. Combined experimental and computational studies enabled a deep understanding of factors controlling the reactivity of both aromatic and aliphatic amine N-oxides.

Highly chemoselective deoxygenation of N-heterocyclic: N -oxides under transition metal-free conditions

Because their site-selective C-H functionalizations are now considered one of the most useful tools for synthesizing various N-heterocyclic compounds, the highly chemoselective deoxygenation of densely functionalized N-heterocyclic N-oxides has received much attention from the synthetic chemistry community. Here, we provide a protocol for the highly chemoselective deoxygenation of various functionalized N-oxides under visible light-mediated photoredox conditions with Na2-eosin Y as an organophotocatalyst. Mechanistic studies imply that the excited state of the organophotocatalyst is reductively quenched by Hantzsch esters. This operationally simple technique tolerates a wide range of functional groups and allows high-yield, multigram-scale deoxygenation. This journal is

Iron-Catalyzed ?±,?-Dehydrogenation of Carbonyl Compounds

An iron-catalyzed α,β-dehydrogenation of carbonyl compounds was developed. A broad spectrum of carbonyls or analogues, such as aldehyde, ketone, lactone, lactam, amine, and alcohol, could be converted to their α,β-unsaturated counterparts in a simple one-step reaction with high yields.

Monomeric vanadium oxide: A very efficient species for promoting aerobic oxidative dehydrogenation of N-heterocycles

Monomeric active species are very interesting in heterogeneous catalysis. In this work, we proposed a method to prepare VOx-NbOy@C catalysts, which involve the one-pot hydrothermal synthesis of inorganic/organic hybrid materials containing V/Nb followed by thermal treatment under a reducing atmosphere. The prepared catalysts were characterized using different techniques, such as high-angle annular dark-field scanning transmission electron microscopy and X-ray absorption fine structure spectroscopy. It was shown that monomeric VOx species were dispersed homogeneously in the catalysts. The VOx-NbOy@C catalysts displayed high performance in the aerobic oxidative dehydrogenation of N-heterocycles to aromatic heterocycles. It was demonstrated that the selectivity of reaction over the catalyst with a very small amount of V (0.07 wt%) was much higher than that over the NbOy@C, and the catalyst also exhibited excellent stability in the reaction. The detailed study indicated that monomeric VO2 species were the most effective for promoting the reaction. This journal is

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.

Visible-light-mediated organoboron-catalysed metal-free dehydrogenation of N-heterocycles using molecular oxygen

The surge of photocatalytic transformation not only provides unprecedented synthetic methods, but also triggers the enthusiasm for more sustainable photocatalysts. On the other hand, oxygen is an ideal oxidant in terms of atom economy and environmental friendliness. However, the poor reactivity of oxygen at the ground state makes its utilization challenging. Herein, a visible-light-induced oxidative dehydrogenative process is disclosed, which uses an organoboron compound as the photocatalyst and molecular oxygen as the sole oxidant.Viathis approach, an array of N-heterocycles have been accessed under metal-free mild conditions, in good to excellent yields.

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.

Superacid-promoted synthesis of quinoline derivatives

A series of vinylogous imines have been prepared from anilines and cinnamaldehydes. These substrates react in superacidic media to provide quinolines and related compounds. A mechanism for the conversion is proposed which involves the cyclization of dicationic superelectrophilic intermediates. Aromatization of the quinoline ring is thought to occur by superacid-promoted elimination of benzene.

MnOx/catechol/H2O: A cooperative catalytic system for aerobic oxidative dehydrogenation of N-heterocycles at room temperature

Amorphous manganese oxide doped by Na+ ion (Na-AMO) was successfully prepared and found to be an efficient heterogeneous catalyst in aerobic oxidative dehydrogenation of N-heterocycles, cooperate with catechol. Na-AMO was fully characterized by XRD, XPS BET H2-TPR, CO2-TPD FT-IR, TEM, SEM and had rich amounts of surface absorbed active oxygen species which are responsible for superior catalytic performance. The synergistic interaction between Na-AMO and catechol makes catalytic system efficient and tolerant, which offers various N-heterocycles in good to excellent yields under mild conditions.

NCP-Type Pincer Iridium Complexes Catalyzed Transfer-Dehydrogenation of Alkanes and Heterocycles?

A series of NCP-type pincer iridium complexes, (RNCCP)IrHCl (2a—2c) and (BQ-NCOP)IrHCl 3, have been studied for catalytic transfer alkane dehydrogenation. Complex 3 containing a rigid benzoquinoline backbone exhibits high activity and robustness in dehydrogenation of alkanes to form alkenes. Even more importantly, this catalyst system was also highly effective in the dehydrogenation of a wide range of heterocycles to furnish heteroarenes.