1463-17-8

Usage

Chemical Properties

Yellow oily liquid

InChI:InChI=1/C11H11N/c1-8-4-3-5-10-7-6-9(2)12-11(8)10/h3-7H,1-2H3

Upstream product

• 75-07-0 acetaldehyde 
• 95-53-4 o-toluidine 
• 123-63-7 paracetaldehyde 
• 107-21-1 ethylene glycol 
• 611-32-5 8-methylquinoline 
• 917-54-4 methyllithium 
• 109-92-2 ethyl vinyl ether 
• 854627-07-9 2,8-dimethyl-1,2,3,4-tetrahydroquinoline 
• 598-32-3 2-hydroxy-3-butene 
• 4389-45-1 3-methylantranilic acid 
• 57772-50-6 2-amino-3-methylbenzyl alcohol 
• 123-42-2 4-Hydroxy-4-methyl-2-pentanone 
• 84902-24-9 2-amino-3-methylbenzaldehyde 
• 18826-95-4 1.3-butanediol 

Downstream Products

• 1446451-49-5 2,2'-(2-phenylpropane-1,3-diyl)bis(8-methylquinoline) 
• 67081-69-0 2-acetylamino-3-methylbenzoic acid 

Relevant academic research and scientific papers

Photocatalytic tandem reaction of primary alcohols with arylamines in the synthesis of amides and alkylquinolines in the presence of a heterogeneous Fe(CrO2)2–TiO2/X system under aerobic conditions

A heterogeneous system Fe(CrO2)2–TiO2/X (where X is promoter NiO, CuO, ZnO, Cr2O3, Fe2O3, PrOCl, TbOCl, LaOCl, or EuOCl) was prepared. The photocatalytic activity of the system was tested in the tandem reaction of primary alcohols (BnOH, EtOH) with arylamines aimed at synthesizing benzamides and substituted 2-methylquinolines under aerobic conditions at room temperature.

Metal-Free Oxidative B?N Coupling of nido-Carborane with N-Heterocycles

A general method for the oxidative substitution of nido-carborane (7,8-C2B9H12?) with N-heterocycles has been developed by using 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) as an oxidant. This metal-free B?N coupling strategy, in both inter- and intramolecular fashions, gave rise to a wide array of charge-compensated, boron-substituted nido-carboranes in high yields (up to 97 %) with excellent functional-group tolerance under mild reaction conditions. The reaction mechanism was investigated by density-functional theory (DFT) calculations. A successive single-electron transfer (SET), B?H hydrogen-atom transfer (HAT), and nucleophilic attack pathway is proposed. This method provides a new approach to nitrogen-containing carboranes with potential applications in medicine and materials.

C-Bridged Bispyrrolidines and Bispiperidines as New Ligands

The preparation of methylene-bridged C2-symmetric nitrogen-heterocycles as a new class of ligands is described, including methylene-bridged pyridines, quinolones, piperidines and pyrrolidines. These methylene-bridged aromatic systems are obtained via a microwave assisted Ziegler-type reaction. The separation of diastereomers and the application of the copper complexes of these ligands for cyclopropanation reactions proves the applicability of these new types of ligands.

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).

Fe(CrO2)2-catalyzed, photoactivated oxidative one-pot tandem synthesis of substituted quinolines from primary alcohols and arylamines

[Figure not available: see fulltext.] A one-pot tandem synthesis of substituted quinolines involving selective catalytic oxidation of primary alcohols to the corresponding aldehydes and their subsequent condensation with arylamines has been developed. Fe(CrO2)2 has been used as a catalyst, and oxidation has been performed with aqueous H2O2. To accelerate the catalytic oxidation of alcohols, photoactivation method has been applied.

One-Pot Oxidative Synthesis of Substituted Quinolines from Alcohols and Arylamines Catalyzed by Fe(CrO2)2 in Water Medium

One-pot tandem synthesis was developed for substituted quinolines (in up to 97% yields) involving a selective catalytic oxidation of primary amines to aldehydes and their condensation with arylamines under the action of a dispersion of Fe(CrO2)2 and water solution of H2O2 at room temperature. The stage of catalytic oxidation of alcohols was accelerated by photoactivation. A presumable mechanism of the photoactivated tandem synthesis of 2-methylquinoline was suggested. Catalyst Fe(CrO2)2 was prepared by photochemical synthesis.

Traceless Directing-Group Strategy in the Ru-Catalyzed, Formal [3 + 3] Annulation of Anilines with Allyl Alcohols: A One-Pot, Domino Approach for the Synthesis of Quinolines

A unique, ruthenium-catalyzed, [3 + 3] annulation of anilines with allyl alcohols in the synthesis of substituted quinolines is reported. The method employs a traceless directing group strategy in the proximal C-H bond activation and represents a one-pot Domino synthesis of quinolines from anilines.

Assembly of Diversely Substituted Quinolines via Aerobic Oxidative Aromatization from Simple Alcohols and Anilines

An aerobic oxidative aromatization of simple aliphatic alcohols and anilines under the Pd(OAc)2/2,4,6-Collidine/Br?nsted acid catalytic system has been established, providing a direct approach for the preparation of diverse substituted quinoline derivatives in high yields with wide functional group tolerance. Practically, the protocol can be easily scaled up to gram-scale and was utilized in the concise formal synthesis of a promising herbicide candidate.

Preparation method of quinoline derivative

The invention provides a preparation method of a quinoline derivative. The method includes the steps of: in the presence of an oxidizing agent, adding a catalyst, then adding aniline or aromatic amine with different substituents, at the same time adding alcohol for reaction so as to prepare the quinoline derivative by one step. Specifically, the catalyst comprises a metal catalyst, an assistant catalyst I and an assistant catalyst II; the metal catalyst is a transition metal catalyst; the assistant catalyst I is an alkaline nitrogen-containing ligand; and the assistant catalyst II is an acidic compound. The quinoline derivative prepared by the method provided by the invention has stable performance and high purity. And the preparation method of the quinoline derivative can prepare quinoline, 2-methylquinoline, 8-hydroxyquinoline quinoline and other derivatives by one-step reaction, and the preparation method is simple and practicable. The preparation process does not produce new "three wastes", is environment-friendly, and provides a green and environment-friendly synthesis method. The preparation method has the characteristics of few raw material variety, little reaction equipment, few preparation step and low cost, and is more suitable for industrial production.

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.