15785-08-7

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
2-METHYL-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER is used as a building block in the synthesis of pharmaceuticals and agrochemicals due to its potential biological and pharmacological activities. It serves as an important intermediate in the development of new drugs, contributing to the creation of innovative treatments and products.
Used in the Food Industry:
In the food industry, 2-METHYL-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER is used as a flavoring agent. Its unique properties allow it to enhance the taste and aroma of various food products, adding value to the final consumer experience.

InChI:InChI=1/C13H13NO2/c1-3-16-13(15)11-8-10-6-4-5-7-12(10)14-9(11)2/h4-8H,3H2,1-2H3

Upstream product

• 55857-35-7 (E)-N-(2-aminobenzylidene)-4-methylaniline 
• 141-97-9 ethyl acetoacetate 
• 529-23-7 o-aminobenzaldehyde 
• 67-56-1 methanol 
• 79237-43-7 1,1-Diethoxy-1,2-dihydro-cyclobuta[b]quinoline 
• 104765-27-7 2-(2-Nitrobenzyliden)acetessigsaeureethylester 
• 104765-27-7 ethyl-2-(2-nitrobenzyliden)acetoacetate 
• 21835-65-4 4-(2-aminophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid diethyl ester 
• 79237-42-6 1,1-dimethoxy-1,2-dihydrocyclobutaquinoline 
• 125836-45-5 2-Cyano-quinoline-3-carboxylic acid ethyl ester 
• 75-65-0 tert-butyl alcohol 
• 108139-81-7 4,6-dimethyl-2-(2-nitrophenyl)-1,2-dihydropyridine-3,5-dicarboxylic acid diethyl ester 
• 552-89-6 2-nitro-benzaldehyde 
• 50741-46-3 ethyl 3-quinolinecarboxylate 

Downstream Products

• 134340-92-4 2-methylquinoline-3-carbohydrazide 
• 53936-95-1 3-(hydroxymethyl)-2-methylquinoline 
• 635-79-0 2-methylquinoline-3-carboxylic acid 

Relevant academic research and scientific papers

TBAHS-catalyzed synthesis of 2-dihydroquinazolin-2-ylquinoline: An efficient and practical synthesis of naturally occurring alkaloids luotonin A, B, and e

A synthesis of 2-dihydroquinazolin-2-ylquinoline using a phase-transfer catalyst (TBAHS) in semi-aqueous phase, followed by Mitsunobu cyclization as key steps for an efficient and practical synthesis of naturally occurring alkaloids luotonin A, B, and E starting from o-nitrobenzaldehyde is reported. The new approach presents the advantage of a shorter route with high overall yield (57%, 45%, and 37%, respectively) and ease of operation.

Lewis Acid-Catalyzed C(sp3)–C(sp3) Bond Forming Cyclization Reactions for the Synthesis of Tetrahydroprotoberberine Derivatives

An efficient Lewis acid-catalyzed C(sp3)–C(sp3) bond forming annulation reaction has been developed. This strategy serves as a new method for the facile synthesis of tetrahydro-5H-isoquinolino[2,1-g][1,6]naphthyridine derivatives. A wide range of 2-methylquinoline-3-carbaldehydes and 1,2,3,4-tetrahydroisoquinolines can be applied for this process to afford structurally diverse tetrahydroprotoberberine derivatives in excellent yields. (Figure presented.).

A NOVEL PHOTO-INDUCED SUBSTITUTION OF ALKYL 2-CYANO-3-QUINOLINECARBOXYLATES

Irradiation of 2-quinolinecarbonitriles having an alkoxycarbonyl group at the 3-position afforded five-membered and/or six-membered lactones in normal alcohols depending on their alkyl-chain-length, whereas the irradiation in 2-propanol and t-butyl alcohol did not cause any cyclization, but instead decyanated and methylated products were obtained, respectively.

Palladium(II)-Catalyzed ortho-Arylation of Aromatic Alcohols with a Readily Attachable and Cleavable Molecular Scaffold

A palladium(II)-catalyzed C?H arylation process of alcohols has been developed. The strategy utilizes a novel quinoline-based hemiacetal scaffold that can direct the selective C?H bond functionalization. This reaction provides a useful method to construct biaryl compounds of benzyl alcohols in good to excellent yields. The new molecular scaffold can be readily attached, removed, and recovered.

A novel Gcn5p inhibitor represses cell growth, gene transcription and histone acetylation in budding yeast

Histone acetyltransferases are key chromatin regulators responsible for transcriptional activation and cell cycle progression. We propose a simple yeast-based assay to determine the specificity and targets of novel Gcn5p inhibitors. Here, we report the finding of a novel, small molecule, MC1626, which is able to inhibit yeast cell growth, Gcn5p-dependent gene transcription and acetylation of the histone H3 N-terminal tail in vivo. Because HATs misregulation is invariably associated with human diseases, the identification of MC1626 as a novel cell-permeable Gcn5p inhibitor suggests that it may be a very useful starting tool for the further development of new molecules to be applied to expression profiling of genes regulated by histone H3 acetylation. In addition, our results demonstrate that MC1626 is a Gcn5p-dependent yeast growth inhibitor.

An efficient heterogeneous gold(I)-catalyzed intermolecular cycloaddition of 2-aminoaryl carbonyls and internal alkynes leading to polyfunctionalized quinolines

The first heterogeneous intermolecular cycloaddition of 2-aminoaryl carbonyls and internal alkynes was realized in DMF at 100 °C by using a triphenylphosphine-functionalized MCM-41-supported gold(I) complex [MCM-41-PPh3-AuCl] and AgOTf as catal

Cascade Knoevenagel and aza-Wittig reactions for the synthesis of substituted quinolines and quinolin-4-ols

A [4 + 2] annulation involving cascade Knoevenagel, aza-Wittig and dehydrofluorination reactions is developed for the synthesis of substituted quinolin-4-ols including analogs bearing CF2H, CF3, and C2F5 groups. This simple and highly efficient method is also applicable for the synthesis of substituted quinolines. A number of reported biologically active compounds can be readily prepared by this one-pot synthesis. Green chemistry metrics analysis of the new reaction processes provided favorable results.

Synthesis of Polysubstituted Quinolines from α-2-Aminoaryl Alcohols Via Nickel-Catalyzed Dehydrogenative Coupling

This study reports a nickel-catalyzed sustainable synthesis of polysubstituted quinolines from α-2-aminoaryl alcohols by a sequential dehydrogenation and condensation process that offers the advantages of a low catalyst loading and wide substrate scope. In contrast to earlier reported methods, this strategy allows the use of both primary as well as secondary α-2-aminoaryl alcohols in combination with either ketones or secondary alcohols for desired product formation. Using this methodology, 30 substituted quinoline derivatives were synthesized with up to 93% isolated yields.

Asymmetric synthesis of isoquinolinonaphthyridines catalyzed by a chiral Br?nsted acid

A catalytic asymmetric method for the synthesis of chiral isoquinolinonaphthyridines has been developed. A chiral disulfonimide catalyzes a redox cyclization reaction between 2-methyl-3-aldehydeazaarenes and 1,2,3,4-tetrahydroisoquinolines to deliver a range of isoquinolinonaphthyridines with good to high yields (up to 91%) and up to 92:8 er.

Photochemistry of ortho -Azidocinnamoyl Derivatives: Facile and Modular Synthesis of 2-Acylated Indoles and 2-Substituted Quinolines under Solvent Control

The light-promoted potential of ortho -azidocinnamoyl compounds is evaluated for heterocycle synthesis. Depending on the nature of the solvent, 2-acylated indoles were obtained under aprotic conditions, whereas the use of a protic medium led to 2-substituted quinolines. The synthetic significance of this metal-free method is that, by simply changing the solvent, the reaction outcome can be directed towards different key heterocyclic scaffolds.