802255
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
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Assay:
95%
Form:
powder
Product Name
8-Amino-5-methoxyquinoline, 95%
InChI
1S/C10H10N2O/c1-13-9-5-4-8(11)10-7(9)3-2-6-12-10/h2-6H,11H2,1H3
SMILES string
NC1=CC=C(OC)C2=CC=CN=C21
InChI key
MFLLTRMMFHENCM-UHFFFAOYSA-N
assay
95%
form
powder
mp
90-95 °C
Quality Level
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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.
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.
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Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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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)
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
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