802255

8-Amino-5-methoxyquinoline

95%

• Synonym(s): 5-Methoxy-8-quinolinamine, Chen Auxilliary, MQ, Gong Chen Auxiliary, MQ Auxiliary
• Empirical Formula (Hill Notation): C₁₀H₁₀N₂O
• CAS Number: 30465-68-0
• Molecular Weight: 174.20
• NACRES: NA.22
• PubChem Substance ID: 329768733
• UNSPSC Code: 12352100
• MDL number: MFCD01593679
• Assay: 95%
• Form: powder

Properties

• Quality Segment: 100
• 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

Description

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.[1] These properties have been useful for synthesizing isomeric dibenzoxazepinones and complex pyrrolidinones from compounds containing 8-amino-5-methoxyquinoline moiety.[1]

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.

Other Notes

Use of a Readily Removable Auxiliary Group for the Synthesis of Pyrrolidones by the Palladium-Catalyzed Intramolecular Amination of Unactivated γ C(sp³)-H bonds

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• 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