54197-64-7

Basic information

• Product Name: 6-Methoxy-3,4-dihydro-1H-quinolin-2-one
• Synonyms: 6-METHOXY-2-OXO-1,2,3,4-TETRAHYDROQUINILINE;6-METHOXY-3,4-DIHYDRO-1H-QUINOLIN-2-ONE;6-METHOXY-3,4-DIHYDRO-2(1H)-QUINOLINONE;6-Methoxy-3,4-dihydro-1H-quinolin-2-one 98%;6-METHOXY-3,4-DIHYDROQUINOLIN-2-ONE;2(1H)-Quinolinone, 3,4-dihydro-6-methoxy-;6-Methoxy-3,4-dihydro-1H-quinolin-2-one98%
• CAS NO: 54197-64-7
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.2
• Mol File: 54197-64-7.mol
• Article Data: 24

Chemical Properties

• Melting Point: 160-161 °C(Solv: water (7732-18-5); methanol (67-56-1))
• Boiling Point: 375.078ºC at 760 mmHg
• Flash Point: 180.641ºC
• Appearance: /
• Density: 1.16g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.549
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.24±0.20(Predicted)
• CAS DataBase Reference: 6-Methoxy-3,4-dihydro-1H-quinolin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Methoxy-3,4-dihydro-1H-quinolin-2-one(54197-64-7)
• EPA Substance Registry System: 6-Methoxy-3,4-dihydro-1H-quinolin-2-one(54197-64-7)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• Hazardous Substances Data: 54197-64-7(Hazardous Substances Data)

Usage

General Description

6-Methoxy-3,4-dihydro-1H-quinolin-2-one, also known as 2-methoxy-3,4-dihydroquinolin-1(2H)-one, is a chemical compound with a molecular formula C10H11NO2. It belongs to the class of organic compounds known as 3,4-dihydro-2H-1-benzopyran-2-ones. 6-Methoxy-3,4-dihydro-1H-quinolin-2-one is a white solid and is soluble in water. It is a derivative of quinolin-2(1H)-one and is commonly used in the synthesis of pharmaceuticals and fine chemicals due to its potential pharmacological properties. 6-Methoxy-3,4-dihydro-1H-quinolin-2-one has been reported to exhibit antimicrobial and anti-inflammatory activities. Additionally, it has been studied for its potential as an inhibitor of aldose reductase, an enzyme involved in diabetic complications.

InChI:InChI=1/C10H11NO2/c1-13-8-3-4-9-7(6-8)2-5-10(12)11-9/h3-4,6H,2,5H2,1H3,(H,11,12)

Upstream product

• 54197-66-9 3,4-dihydro-6-hydroxy-2(1H)-quinolinone 
• 74-88-4 methyl iodide 
• 113961-91-4 1-Hydroxy-6-methoxy-3,4-dihydroquinolin-2(1H)-one 
• 77-78-1 dimethyl sulfate 
• 120-15-0 6-methoxy-1,2,3,4-tetrahydroquinoline 
• 125810-71-1 methyl 3-(5-methoxy-2-nitrophenyl)acrylate 
• 1493774-34-7 methyl 3-(5-methoxy-2-nitrophenyl)propanoate 
• 140-88-5 ethyl acrylate 
• 191348-14-8 2-iodo-4-methoxylaniline 
• 457622-19-4 3-(2-amino-5-methoxyphenyl)-1-propanol 
• 10226-40-1 5-methoxy-2-nitrocinnamic acid 
• 91523-37-4 N-methoxy-3,4-dihydro-1H-quinolin-2-one 
• 10226-40-1 5-methoxy-2-nitrocinnamic acid 
• 40478-49-7 3-(3-methoxyphenyl)propanoyl chloride 

Downstream Products

• 120-15-0 6-methoxy-1,2,3,4-tetrahydroquinoline 
• 91957-45-8 1-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)prop-2-en-1-one 
• 1215765-65-3 1-(4-methoxybenzyl)-3,4-dihydro-6-methoxyquinolin-2(1H)-one 
• 1217436-63-9 6-methoxy-1-(3-phenylprop-2-ynyl)-3,4-dihydroquinolin-2-(1H)-one 
• 115706-38-2 2-(1,2,3,4-tetrahydro-2-oxo-6-methoxyquinolin-1-yl)propionic acid 

Relevant articles and documents

Ruthenium-catalyzed intramolecular arene C(sp2)-H amidation for synthesis of 3,4-dihydroquinolin-2(1 H)-ones

We report the [Ru(p-cymene)(l-proline)Cl] ([Ru1])-catalyzed cyclization of 1,4,2-dioxazol-5-ones to form dihydroquinoline-2-ones in excellent yields with excellent regioselectivity via a formal intramolecular arene C(sp2)-H amidation. The reactions of the 2- and 4-substituted aryl dioxazolones proceeds initially through spirolactamization via electrophilic amidation at the arene site, which is para or ortho to the substituent. A Hammett correlation study showed that the spirolactamization is likely to occur by electrophilic nitrenoid attack at the arene, which is characterized by a negative ρ value of -0.73.

Synthesis of Lactams via Ir-Catalyzed C-H Amidation Involving Ir-Nitrene Intermediates

x-membered lactams were synthesized via either an amidation of sp3 C-H bonds or an electrophilic substitution of arenes via Ir-nitrene intermediates. With the employment of a readily available iridium catalyst in dichloromethane or hexafluoro-2-propanol, a wide range of lactams were synthesized in good to excellent yields with high selectivity.

Revisiting Arene C(sp2)?H Amidation by Intramolecular Transfer of Iridium Nitrenoids: Evidence for a Spirocyclization Pathway

Two mechanistic pathways, that is, electrocyclization and electrophilic aromatic substitution, are operative in most intramolecular C?H amination reactions proceeding by metal nitrenoid catalysis. Reported here is an alternative mechanistic scaffold leading to benzofused δ-lactams selectively. Integrated experimental and computational analysis revealed that the reaction proceeds by a key spirocyclization step followed by a skeletal rearrangement. Based on this mechanistic insight, a new synthetic route to spirolactams has been developed.