10562-04-6

Basic information

• Product Name: 2-Quinolinamine, 4-methyl-N-phenyl-
• CAS NO: 10562-04-6
• Molecular Formula: C16H14N2
• Molecular Weight: 234.301
• Mol File: 10562-04-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2-Quinolinamine, 4-methyl-N-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Quinolinamine, 4-methyl-N-phenyl-(10562-04-6)
• EPA Substance Registry System: 2-Quinolinamine, 4-methyl-N-phenyl-(10562-04-6)

Safety Data

• Hazardous Substances Data: 10562-04-6(Hazardous Substances Data)

Upstream product

• 634-47-9 2-chloro-4-methylquinoline 
• 62-53-3 aniline 
• 103264-22-8 4-methyl-quinoline-2-sulfonic acid 
• 52562-19-3 2-isopropenylaniline 
• 103-72-0 phenyl isothiocyanate 
• 607-66-9 4-methyl-1,2-dihydroquinolin-2-one 
• 607-66-9 4-methylquinolin-2-ol 
• 10562-00-2 4,4-bis(phenylamino)but-3-en-2-one 

Downstream Products

• 78541-69-2 (1,4-dimethyl-1H-[2]quinolylidene)-phenyl-amine; hydriodide 

Relevant articles and documents

Robust Acenaphthoimidazolylidene Palladacycles: Highly Efficient Catalysts for the Amination of N-Heteroaryl Chlorides

A series of robust N-heterocyclic carbene palladacycles have been successfully developed. These showed high catalytic activity and selectivity toward the challenging amination of N-heteroaryl chlorides. Different primary and secondary amines were fully compatible with this catalytic system. Remarkably, no double amination products could be detected when primary amines were utilized in our catalytic transformation. Furthermore, the protocol has been successfully extended to synthesize rosiglitazone, a clinical drug for diabetes mellitus, highlighting its potential pharmaceutical feasibility.

Cu-catalyzed aerobic oxidative cyclizations of 3-N-hydroxyamino-1,2-propadienes with alcohols, thiols, and amines to form α-O-, S-, and N-substituted 4-methylquinoline derivatives

A one-pot, two-step synthesis of α-O-, S-, and Nsubstituted 4-methylquinoline derivatives through Cu-catalyzed aerobic oxidations of N-hydroxyaminoallenes with alcohols, thiols, and amines is described. This reaction sequence involves an initial oxidation of N-hydroxyaminoallenes with NuH (Nu = OH, OR, NHR, and SR) to form 3-substituted 2-en-1-ones, followed by Bronsted acid catalyzed intramolecular cyclizations of the resulting products. Our mechanistic analysis suggests that the reactions proceed through a radical-type mechanism rather than a typical ni-trone-intermediate route. The utility of this new Cu-catalyzed reaction is shown by its applicability to the synthesis of several 2-amino-4-methylquinoline derivatives, which are known to be key precursors to several bioactive molecules.

Synthesis of dibenzo(b,g)-5-methyl-1,8-naphthyridines

A series of 1,8-naphthyridines have been synthesised. 2-Hydroxy-4-methylquinoline 1 on reaction with PCI5/POCl3 gives 2-chloro-4-methylquinoline 2 which on treatment with substituted anilines yields 2-quinolinamines 3a-e. Cyclisation in situ affords the title compounds 4a-e using phosphorus oxychloride and dimethyl formamide.