826-77-7

Usage

InChI:InChI=1/C11H11N/c1-8-3-4-11-10(7-8)9(2)5-6-12-11/h3-7H,1-2H3

Upstream product

• 3913-18-6 2-chloro-4,6-dimethylquinoline 
• 50-00-0 formaldehyd 
• 106-49-0 p-toluidine 
• 67-64-1 acetone 
• 103-89-9 4-Methylacetanilide 
• 7647-01-0 hydrogenchloride 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 111831-88-0 N-(3-chloro-but-2-enyl)-p-toluidine 
• 23947-37-7 2-hydroxy-6-methyllepidine 
• 18436-71-0 4-chloro-6-methylquinoline 
• 75-16-1 methylmagnesium bromide 
• 23947-37-7 4,6-dimethylquinolin-2(1H)-one 
• 18826-95-4 1.3-butanediol 
• 1384466-89-0 C₁₆H₂₃NO₃ 

Downstream Products

• 1028758-07-7 6-methyl-4-(4-nitro-trans-styryl)quinoline 
• 7101-68-0 4-methyl-6-quinolinecrboxylic acid 
• 110244-27-4 N,N-dimethyl-4-[trans-2-(6-methyl-[4]quinolyl)-vinyl]-aniline 

Relevant academic research and scientific papers

Metal-Free Chemoselective Oxidation of 4-Methylquinolines into Quinoline-4-Carbaldehydes

A convenient protocol for the synthesis of quinoline-4-carbaldehydes via chemoselective oxidation of 4-methylquinolines using hypervalent iodine(III) reagents as oxidant is described. This method highlights metal-free and mild reaction conditions, nice yield, good functional group tolerance, and high chemoselectivity.

Synthesis and antileishmanial evaluation of thiazole orange analogs

Cyanine compounds have previously shown excellent in vitro and promising in vivo antileishmanial efficacy, but the potential toxicity of these agents is a concern. A series of 22 analogs of thiazole orange ((Z)-1-methyl-4-((3-methylbenzo[d]thiazol-2(3H)-ylidene)methyl)quinolin-1-ium salt), a commercial cyanine dye with antileishmanial activity, were synthesized in an effort to increase the selectivity of such compounds while maintaining efficacy. Cyanines possessing substitutions on the quinolinium ring system displayed potency against Leishmania donovani axenic amastigotes that differed little from the parent compound (IC50 12–42 nM), while ring disjunction analogs were both less potent and less toxic. Changes in DNA melting temperature were modest when synthetic oligonucleotides were incubated with selected analogs (ΔTm ≤ 5 °C), with ring disjunction analogs showing the least effect on this parameter. Despite the high antileishmanial potency of the target compounds, their toxicity and relatively flat SAR suggests that further information regarding the target(s) of these molecules is needed to aid their development as antileishmanials.

Quinolines synthesis by reacting 1,3-butanediol with anilines in the presence of iron catalysts

2-, 4-, 6-, 7-, and 8-substituted quinolines were synthesized in 78–95% yield by the reaction of 1,3- butanediol with anilines in the presence of iron catalysts in carbon tetrachloride.

Efficient synthesis of substituted quinolines through intramolecular addition of aryl anion to carbonyl carbon

Substituted quinolines were synthesized in three steps from the Boc amides of substituted 2-iodoanilines and alkyl vinyl ketones. This method consists of (1) N-Michael addition of the Boc amide of 2-iodoaniline to alkyl vinyl ketone in the presence of Cs2CO3 in MeCN; (2) I-Mg exchange of the adduct with 3.5 equiv of i-PrMgCl·LiCl, and (3) acid-catalyzed reaction (excess AcCl in EtOH) of the resulting alcohol. Six examples are given with good yields.

Solvent-promoted and -controlled Aza-Michael reaction with aromatic amines

(Chemical Equation Presented) 1,4-Addition of anilines onto Michael acceptors proceeds easily in specific polar protic solvents, without any promoting agent. According to the solvent and to the electrophile, the selectivity of the reaction can be finely tuned. With methyl acrylate as electrophile, only monoaddition takes place in water, while the diadduct is yielded in hexafluoroisopropyl alcohol (HFIP). The use of methyl vinyl ketone as a partner affords the monoadduct in water, the diadduct in trifluoroethanol (TFE), and the quinoline in HFIP.

AN IMPROVED PROCESS FOR THE SYNTHESIS OF QUINOLINE DERIVATIVES

The present invention provides an improved process for the synthesis of quinoline derivatives. More particularly the present invention provides an improved and economical process for the synthesis of quinoline derivatives by the reaction of aniline/substituted anilines using two different catalysts, ferric chloride and zinc chloride in a one-pot set up reaction.

Process for the synthesis of quinoline derivatives

The present invention provides an improved process for the synthesis of quinoline derivatives. More particularly the present invention provides an improved and economical process for the synthesis of quinoline derivatives by the reaction of aniline/substituted anilines using two different catalysts, ferric chloride and zinc chloride in a one-pot set up reaction.

High-yielding microwave assisted synthesis of quinoline and dihydroquinoline derivatives under solvent-free conditions

A mild and efficient solvent-free method has been developed by two different approaches for the synthesis of quinoline and dihydroquinoline derivatives: (i) one-pot reaction of anilines with alkyl vinyl ketones (Skraup reaction) (ii) between various acetophenones and 2-aminoacetophenone (Friedlaender reaction) using stable and effective heterogeneous catalyst potassium dodecatangestocobaltate (25 mol %) (PDTC) under microwave irradiation in high yields.

Microwave-assisted simple synthesis of quinolines from anilines and alkyl vinyl ketones on the surface of silica gel in the presence of indium(III) chloride

A simple and efficient procedure has been developed for the synthesis of 4-alkylquinolines by a one-pot reaction of anilines with alkyl vinyl ketones on the surface of silica gel impregnated with indium(III) chloride under microwave irradiation without any solvent.