91133-47-0

Basic information

• Product Name: 2(1H)-Quinolinone, 3,4-dihydro-6,7-dimethoxy-
• Synonyms: 6,7-dimethoxy-1,3,4-trihydroquinolin-2-one;6,7-Dimethoxy-3,4-dihydro-carbostyril;6,7-Dimethoxy-3,4-dihydro-1H-chinolin-2-on
• CAS NO: 91133-47-0
• Molecular Formula: C11H13NO3
• Molecular Weight: 207.229
• Mol File: 91133-47-0.mol

Chemical Properties

• CAS DataBase Reference: 2(1H)-Quinolinone, 3,4-dihydro-6,7-dimethoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(1H)-Quinolinone, 3,4-dihydro-6,7-dimethoxy-(91133-47-0)
• EPA Substance Registry System: 2(1H)-Quinolinone, 3,4-dihydro-6,7-dimethoxy-(91133-47-0)

Safety Data

• Hazardous Substances Data: 91133-47-0(Hazardous Substances Data)

Usage

General Description

2(1H)-Quinolinone, 3,4-dihydro-6,7-dimethoxy- is a chemical compound with the molecular formula C11H13NO3. It is a quinolinone derivative with two methoxy groups attached to the 3 and 4 positions of the ring. 2(1H)-Quinolinone, 3,4-dihydro-6,7-dimethoxy- has been studied for its potential biological activities, including its role as a potential anticancer agent. It has also been investigated for its potential neuroprotective properties and has been found to exhibit anti-inflammatory and antioxidant effects in various in vitro and in vivo studies. Additionally, 2(1H)-Quinolinone, 3,4-dihydro-6,7-dimethoxy- has been evaluated for its potential as a pharmaceutical intermediate in the synthesis of various drugs and other bioactive compounds. Overall, this compound shows promise in various biomedical and pharmaceutical applications.

Upstream product

• 2107-70-2 3,4-methoxycinnamic acid 
• 51842-87-6 3-(3,4-dimethoxy-phenyl)-propionyl chloride 
• 67363-15-9 3-(3,4-dimethoxyphenyl)propanoyl hydroxamic acid 
• 118509-96-9 (E)-3-(4,5-dimethoxy-2-nitro-phenyl)-acrylic acid methyl ester 
• 20357-25-9 6-nitroveratraldehyde 
• 20567-38-8 3.4-dimethoxy-2-nitrocinnamic acid 
• 91958-71-3 ethyl 2-nitro-4,5-dimethoxycinnamate 
• 21164-75-0 3-(4,5-dimethoxy-2-nitro-phenyl)-propionic acid 
• 92042-74-5 3-(4,5-dimethoxy-2-nitro-phenyl)-propionic acid ethyl ester 

Downstream Products

• 1285548-96-0 5-bromo-N-(4-(6,7-dimethoxy-3,4-dihydroquinolin-1(2H)-yl)butyl)-2,3-dimethoxybenzamide 
• 67278-27-7 6,7-Dimethoxy-chinolin 
• 99986-04-6 1,2,3,4-tetrahydro-6,7-dimethoxyquinoline 

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.

Visible-Light Induced C(sp2)?H Amidation with an Aryl–Alkyl σ-Bond Relocation via Redox-Neutral Radical–Polar Crossover

We report an approach for the intramolecular C(sp2)?H amidation of N-acyloxyamides under photoredox conditions to produce δ-benzolactams with an aryl-alkyl σ-bond relocation. Computational studies on the designed reductive single electron transfer strategy led us to identify N-[3,5-bis(trifluoromethyl)benzoyl] group as the most effective amidyl radical precursor. Upon the formation of an azaspirocyclic radical intermediate by the selective ipso-addition with outcompeting an ortho-attack, radical–polar crossover was then rationalized to lead to the rearomative ring-expansion with preferential C?C bond migration.

Room Temperature Benzofused Lactam Synthesis Enabled by Cobalt(III)-Catalyzed C(sp2)?H Amidation

Benzofused lactams, especially indolin-2-one and dihydroquinolin-2-one are popular structural motives in durgs and natural products. Herein, we developed a room temperature and robust synthesis of benzofused lactams through cobalt(III)-catalyzed C(sp

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.

METHOD FOR PRODUCING LACTAM COMPOUND, AND LACTAM COMPOUND PRODUCED THEREBY

The present invention relates to a method for producing a lactam compound from dioxazolone in the presence of a catalyst having a particular ligand, and to a lactam compound produced thereby, and can produce a lactam compound with excellent selectivity and an excellent yield by using the combination of a starting material having a particular functional group and a particular catalyst having a particular ligand.

Selective formation of γ-lactams via C-H amidation enabled by tailored iridium catalysts

Intramolecular insertion of met al nitrenes into carbon-hydrogen bonds to form γ-lactam rings has traditionally been hindered by competing isocyanate formation. We report the application of theory and mechanism studies to optimize a class of pentamethylcyclopentadienyl iridium(III) catalysts for suppression of this competing pathway. Modulation of the stereoelectronic properties of the auxiliary bidentate ligands to be more electron-donating was suggested by density functional theory calculations to lower the C-H insertion barrier favoring the desired reaction. These catalysts transform a wide range of 1,4,2-dioxazol-5-ones, carbonylnitrene precursors easily accessible from carboxylic acids, into the corresponding γ-lactams via sp3 and sp2 C-H amidation with exceptional selectivity. The power of this method was further demonstrated by the successful late-stage functionalization of amino acid derivatives and other bioactive molecules.

IMIDAZOLE COMPOUNDS AS MODULATORS OF FSHR AND USES THEREOF

The present invention relates to imidazole compounds, and pharmaceutically acceptable compositions thereof, useful as positive allosteric modulators of follicle stimulating hormone receptor (FSHR).

Effect of structural modification in the amine portion of substituted aminobutyl-benzamides as ligands for binding σ1 and σ2 receptors

5-Bromo-N-[4-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-butyl)]-2, 3-dimethoxy-benzamide (1) is one of the most potent and selective σ2 receptor ligands reported to date. A series of new analogs, where the amine ring fused to the aromatic ring was varied in size (5-7) and the location of the nitrogen in this ring was modified, has been synthesized and assessed for their σ1/σ2 binding affinity and selectivity. The binding affinity of an open-chained variant of 1 was also evaluated. Only the five-membered ring congener of 1 displayed a higher σ1/σ2 selectivity, derived from a higher σ2 affinity and a lower σ1 affinity. Positioning the nitrogen adjacent to the aromatic ring in the five-membered and six-membered ring congeners dramatically decreased affinity for both subtypes. Thus, location of the nitrogen within a constrained ring is confirmed to be key to the exceptional σ2 receptor binding affinity and selectivity for this active series.

Synthesis of indolones and quinolones by reductive cyclisation of o-nitroaryl acids using zinc dust and ammonium formate

A novel protocol for the synthesis of indolone and quinolone derivatives from o-nitroaryl acids was developed using Zn and HCO2NH4 under supercritical fluid carbon dioxide (scCO2) medium. The process involves the reduction of the nitro group to an amino group followed by in situ cyclisation.