402822-99-5

Basic information

• Product Name: Quinoline, 1-acetyl-1,2-dihydro-4-methyl- (9CI)
• Synonyms: Quinoline, 1-acetyl-1,2-dihydro-4-methyl- (9CI)
• CAS NO: 402822-99-5
• Molecular Formula: C₁₂H₁₃NO
• Molecular Weight: 0
• Mol File: 402822-99-5.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Quinoline, 1-acetyl-1,2-dihydro-4-methyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Quinoline, 1-acetyl-1,2-dihydro-4-methyl- (9CI)(402822-99-5)
• EPA Substance Registry System: Quinoline, 1-acetyl-1,2-dihydro-4-methyl- (9CI)(402822-99-5)

Safety Data

• Hazardous Substances Data: 402822-99-5(Hazardous Substances Data)

Upstream product

• 22514-60-9 1,2-dihydrolepidine 
• 108-24-7 acetic anhydride 
• 402822-95-1 N-allyl-N-acetyl-2-isopropenylaniline 
• 72934-86-2 N-[2-(1-methylethenyl)phenyl]acetamide 
• 52562-19-3 2-isopropenylaniline 
• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 75-36-5 acetyl chloride 

Downstream Products

• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 50459-98-8 4-Methyl-3-phenylquinoline 

Relevant articles and documents

Iridium-catalyzed selective 1,2-hydrosilylation of N-heterocycles

A silylene-bridged Ir dimer in situ generated from [Ir(coe)2Cl]2 and Et2SiH2 was found to catalyze the hydrosilylation of N-heteroaromatics to furnish dearomatized azacyclic products with high activity (up to 1000 TONs), excellent selectivity, and good functional group tolerance. The substrate scope was highly broad, including (iso)quinolines, substituted pyridines, pyrimidines, pyrazines, deazapurines, triazines, and benzimidazoles. Mechanistic studies such as a kinetic profile, rate-order assessment, and investigation of the electronic substituent effects on the initial rates were performed to access the detailed pathways. One pathway is proposed to involve an intramolecular insertion of the CN moiety of the substrates into the Ir-H bond of a resting species to form an Ir-amido silyl intermediate, followed by reductive elimination. The synthetic utility was proven by successful application to cinchona alkaloids, and facile post-synthetic transformations of the 1,2-dihydroquinoline products.

A novel synthesis of substituted quinolines using ring-closing metathesis (RCM): Its application to the synthesis of key intermediates for anti-malarial agents

A method for synthesizing substituted quinolines using ruthenium-catalyzed ring-closing metathesis as a key step has been developed. Substituted 1,2-dihydroquinolines, 4-silyloxy-1,2-dihydroquinoline and 4-methoxy-1,2- dihydroquinoline, were successfully synthesized in excellent yields via ene-ene metathesis and silyl or alkyl enol ether-ene metathesis, respectively. The synthetic intermediates of the antimalarial agents quinine, chloroquine, and PPMP-quinine hybrid were efficiently synthesized by this methodology.

Synthesis of substituted 1,2-dihydroquinolines and quinolines using ene-ene metathesis and ene-enol ether metathesis

We describe a novel and convenient method for quinoline synthesis using ring-closing olefin metathesis (RCM), ene-ene metathesis, and ene-enol ether metathesis. We also report the first example of enol silyl ether-ene metathesis to produce cyclic enol silyl ether. Using this method, versatile substituted quinoline derivatives were readily prepared in excellent yield from anthranilic acid derivatives.