17507-03-8

Basic information

• Product Name: Dimethyl 2,3-quinolinedicarboxylate
• Synonyms: dimethyl 2,3-quinolinedicarboxylate;2,3-quinolinedicarboxylic acid dimethyl ester;acridinic acid;Dimethyl quinoline-2,3-dicarboxylate;2,3-diMethyl quinoline-2,3-dicarboxylate
• CAS NO: 17507-03-8
• Molecular Formula: C₁₃H₁₁NO₄
• Molecular Weight: 245.23
• Mol File: 17507-03-8.mol
• Article Data: 16

Chemical Properties

• Melting Point: 107-108°C
• Boiling Point: 342°C
• Flash Point: 160.8°C
• Appearance: /
• Density: 1.273
• Vapor Pressure: 7.61E-05mmHg at 25°C
• Refractive Index: 1.598
• CAS DataBase Reference: Dimethyl 2,3-quinolinedicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl 2,3-quinolinedicarboxylate(17507-03-8)
• EPA Substance Registry System: Dimethyl 2,3-quinolinedicarboxylate(17507-03-8)

Safety Data

• Hazardous Substances Data: 17507-03-8(Hazardous Substances Data)

Usage

General Description

Dimethyl 2,3-quinolinedicarboxylate is a chemical compound that features a quinoline core, a type of heterocyclic aromatic organic compound. Dimethyl 2,3-quinolinedicarboxylate is further characterized by the presence of two carboxylate groups attached at the 2nd and 3rd positions of the quinoline core, and these groups are in turn modified by methyl groups, giving it the name "dimethyl." It is used extensively in the field of synthetic organic chemistry, as it can serve as a precursor to a variety of other chemical species. Exact properties such as toxicity or reactivity may depend on the specific conditions and reagents it is subjected to.

InChI:InChI=1/C13H11NO4/c1-17-12(15)9-7-8-5-3-4-6-10(8)14-11(9)13(16)18-2/h3-7H,1-2H3

Upstream product

• 25007-54-9 Dimethyl 2-oxosuccinate 
• 529-23-7 o-aminobenzaldehyde 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 271-61-4 benzo[c]isothiazole 
• 74-88-4 methyl iodide 
• 552-89-6 2-nitro-benzaldehyde 
• 4916-29-4 dimethyl 2-(phenyl-amino)-2-butendioate 
• 5344-90-1 2-Aminobenzyl alcohol 
• 27652-35-3 (E)-2-styrylaniline 
• 16714-25-3 2-azidobenzaldehyde 
• 624-49-7 dimethylfumarate 
• 13066-19-8 2-(2-phenylethenyl)benzenamine 
• 67-56-1 methanol 
• 643-38-9 quinoline-2,3-dicarboxylic acid 

Downstream Products

• 57032-14-1 2-hydroxymethyl-quinolin-3-yl-methanol 
• 31456-25-4 camptothecin 
• 156969-70-9 Benzoic acid 4-ethyl-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-4-yl ester 
• 156969-69-6 Benzoic acid 5-(1,3-dihydro-pyrrolo[3,4-b]quinoline-2-carbonyl)-3-ethyl-4-formyl-2-oxo-3,6-dihydro-2H-pyran-3-yl ester 

Relevant articles and documents

Cyclic hydrazides 1. Synthesis of 4-hydroxy-1-oxo-1,2-dihydropyridazino[4,5-b]quinolines

A series of dimethyl esters and cyclic hydrazides of quinoline-2,3-dicarboxylic acid has been synthesized with different substituents in the benzene ring.

Regioselective Cyanation of Six-Membered N-Heteroaromatic Compounds Under Metal-, Activator-, Base- and Solvent-Free Conditions

A regioselective cyanation of heteroaromatic N-oxides with trimethylsilyl cyanide has been developed to obtain 2-substituted N-heteroaromatic nitrile without the requirement of any external activator-, metal-, base-, and solvent. The present protocol is a straightforward, one-pot heteroaromatic C?H cyanation process, and proceeds smoothly in conventional heating but also under microwave irradiation with shorter reaction times. This approach now allows access to a broad class of quinoline N-oxides and other heteroarene N-oxides with high to good yields and can also be scaled up to obtain gram quantities. Further application of this process was observed and utilized in late-stage cyanation of the anti-malarial drug quinine as well as transformation of the 2-cyanoazines to a series of biologically important molecules. Based on the experimental observations, a plausible mechanism has also been proposed highlighting the dual role of trimethylsilyl cyanide as a nitrile source and as an activating agent. (Figure presented.).

Visible-Light Induced and Oxygen-Promoted Oxidative Cyclization of Aromatic Enamines for the Synthesis of Quinolines Derivatives

The dual transition metal-visible light photoredox catalysis for the synthesis of quinoline derivatives by using dioxygen as an oxygen source is developed. By using visible light, the direct oxidative cyclization of aromatic enamines with alkynes or alkenes can be achieved at mild conditions with an aid of copper or palladium catalysts, and a variety of multisubstituted quinoline derivatives could be obtained in good to moderate yields under mild reaction conditions.