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54197-64-7

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54197-64-7 Usage

Description

6-Methoxy-3,4-dihydro-1H-quinolin-2-one, also known as 2-methoxy-3,4-dihydroquinolin-1(2H)-one, is a white solid chemical compound with the molecular formula C10H11NO2. It belongs to the class of organic compounds known as 3,4-dihydro-2H-1-benzopyran-2-ones and is soluble in water. As a derivative of quinolin-2(1H)-one, it is commonly used in the synthesis of pharmaceuticals and fine chemicals due to its potential pharmacological properties.

Uses

Used in Pharmaceutical Synthesis:
6-Methoxy-3,4-dihydro-1H-quinolin-2-one is used as an intermediate in the synthesis of pharmaceuticals and fine chemicals for its potential pharmacological properties.
Used in Antimicrobial Applications:
6-Methoxy-3,4-dihydro-1H-quinolin-2-one is used as an antimicrobial agent, exhibiting activity against various microorganisms, which makes it a valuable compound in the development of new antimicrobial drugs.
Used in Anti-inflammatory Applications:
6-Methoxy-3,4-dihydro-1H-quinolin-2-one is used as an anti-inflammatory agent, demonstrating the ability to reduce inflammation, which can be beneficial in the treatment of various inflammatory conditions.
Used in Diabetic Complications Management:
6-Methoxy-3,4-dihydro-1H-quinolin-2-one is studied for its potential as an inhibitor of aldose reductase, an enzyme involved in diabetic complications. Its use as an aldose reductase inhibitor could help in managing and treating complications associated with diabetes.

Check Digit Verification of cas no

The CAS Registry Mumber 54197-64-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,4,1,9 and 7 respectively; the second part has 2 digits, 6 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 54197-64:
(7*5)+(6*4)+(5*1)+(4*9)+(3*7)+(2*6)+(1*4)=137
137 % 10 = 7
So 54197-64-7 is a valid CAS Registry Number.
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)

54197-64-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 6-Methoxy-3,4-dihydro-1H-quinolin-2-one

1.2 Other means of identification

Product number -
Other names 6-Methoxy-2-oxo-1,2,3,4-tetrahydro-quinoline

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:54197-64-7 SDS

54197-64-7Relevant articles and documents

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

Au, Chi-Ming,Ling, Cho-Hon,Sun, Wenlong,Yu, Wing-Yiu

, p. 3310 - 3314 (2021/05/29)

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

Li, Xiaoxun,Liu, Jitian,Tang, Weiping,Wang, Shuojin,Ye, Wenjing,Zheng, Junrong

, (2020/03/19)

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.

Enabling CO Insertion into o-Nitrostyrenes beyond Reduction for Selective Access to Indolin-2-one and Dihydroquinolin-2-one Derivatives

Yang, Li,Shi, Lijun,Xing, Qi,Huang, Kuo-Wei,Xia, Chungu,Li, Fuwei

, p. 10340 - 10348 (2018/10/20)

The transition metal-catalyzed reductive cyclization of o-nitrostyrene in the presence of carbon monoxide (CO) has been developed to be a general synthetic route to an indole skeleton, wherein CO was used as a reductant to deoxidize nitroarene into nitrosoarene and/or nitrene with CO2 release, but the selective insertion of CO into the heterocyclic product with higher atom economy has not yet been realized. Herein, the Pd-catalyzed reduction of o-nitrostyrene by CO and its regioselective insertion were efficiently achieved to produce synthetically useful five- and six-membered benzo-fused lactams. Detailed investigations revealed that the chemoselectivity to indole or lactam was sensitive to the nature of the counteranions of Pd2+ precursors, whereas ligands significantly decided the carbonylative regioselectivity by different reaction pathways. Using PdCl2/PPh3/B(OH)3 (condition A), an olefin hydrocarboxylation was primarily initiated followed by partial reduction of the NO2 moiety and cyclization reaction to give N-hydroxyl indolin-2-one, which was further catalytically reduced by CO to afford the indolin-2-one as the final product with up to 95% yield. When the reaction was conducted under the Pd(TFA)2/BINAP/TsOH·H2O system (condition B), complete deoxygenation and carbonylation of the NO2 group occurred initially to yield the corresponding isocyanate followed by internal hydrocyclization to generate 3,4-dihydroquinolin-2-one with up to 98% yield. Importantly, the methodology could be efficiently applied in the synthesis of marketed drug Aripiprazole.

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