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802255

Sigma-Aldrich

8-Amino-5-methoxyquinoline

95%

Synonym(s):

5-Methoxy-8-quinolinamine, Chen Auxilliary, MQ, Gong Chen Auxiliary, MQ Auxiliary

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About This Item

Empirical Formula (Hill Notation):
C10H10N2O
CAS Number:
Molecular Weight:
174.20
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

95%

form

powder

mp

90-95 °C

SMILES string

NC1=CC=C(OC)C2=CC=CN=C21

InChI

1S/C10H10N2O/c1-13-9-5-4-8(11)10-7(9)3-2-6-12-10/h2-6H,11H2,1H3

InChI key

MFLLTRMMFHENCM-UHFFFAOYSA-N

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General description

8-Amino-5-methoxyquinoline is a substituted quinoline derivative that can be prepared using 5-chloro-2-nitroaniline as a starting material. It can act as an easily removable directing group and also mediate C-H activation. These properties have been useful for synthesizing isomeric dibenzoxazepinones and complex pyrrolidinones from compounds containing 8-amino-5-methoxyquinoline moiety.

Application

The Chen auxiliary was reported to be an effective directing group in the synthesis of pyrrolidones from assisting in the activation of C(sp3)-H bonds and can be readily installed through amide bond formation and removed through mild conditions using CAN at room temperature.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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Yunfei Zhou et al.
Organic letters, 18(3), 380-383 (2016-01-16)
An efficient new way to access two regio-isomeric dibenzoxazepinones is reported from 8-aminoquinoline benzamides and 2-bromophenols. Through choice of conditions, the reaction proceeds either through a sequential C-H etherification and subsequent Goldberg reaction, both controlled by the aminoquinoline group and
Use of a Readily Removable Auxiliary Group for the Synthesis of Pyrrolidones by the Palladium-Catalyzed Intramolecular Amination of Unactivated ? C(sp3)-H Bonds.
He G, et al.
Angewandte Chemie (Weinheim an der Bergstrasse, Germany), 125(42), 11330-11334 (2013)

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