104785-55-9

Usage

Chemical Properties

White solid

InChI:InChI=1/C12H11NO2/c1-7-9-5-3-4-6-10(9)13-8(2)11(7)12(14)15/h3-6H,1-2H3,(H,14,15)/p-1

Upstream product

• 859959-35-6 2,4-dimethylquinoline-3-carbonitrile 
• 104785-54-8 2,4-dimethylquinoline-3-carboxylic acid ethyl ester 
• 141-97-9 ethyl acetoacetate 
• 551-93-9 2-aminoacetophenone 
• 105-45-3 acetoacetic acid methyl ester 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 104785-56-0 11R-3-(N-α-methylbenzyl)carbamoyl-2,4-dimethylquinoline 
• 104785-59-3 (13S)-1,2,4-trimethyl-3-(N-α-methylbenzylcarbamoyl)quinolinium iodide 
• 104785-63-9 1,2,4-Trimethyl-3-[methyl-((R)-1-phenyl-ethyl)-carbamoyl]-quinolinium; iodide 
• 104785-59-3 11R-3-(N-α-methylbenzyl)carbamoyl-1,2,4-trimethylquinolinium iodide 
• 104465-71-6 4S,11R-3-(N-methyl-N-α-methylbenzyl)carbamoyl-1,2,4-trimethyl-1,4-dihydroquinoline 
• 104785-60-6 4S,11S-3-(N-α-methylbenzy)carbamoyl-1,2,4-trimethyl-1,4-dihydroquinoline 
• 104785-57-1 (4R)-3-(N-(R)-α-methylbenzylcarbamoyl)-1,2,4-trimethyl-1,4-dihydroquinoline 
• 83670-13-7 3-(N-(R)-α-methylbenzylcarbamoyl)-1,2,4-trimethyl-1,4-dihydroquinoline 
• 104465-70-5 (4R)-3--1,2,4-trimethyl-1,4-dihydroquinoline 

Relevant academic research and scientific papers

Microwave-assisted Friedl?nder synthesis of quinolines derivatives as potential antiparasitic agents

A series of substituted quinolines was developed via the Friedl?nder reaction employing microwave irradiation (MW), in the presence of a catalytic amount of hydrochloric acid. The products were obtained in good yields in 1.5-12 min and were tested in vitr

A hydrazine functionalized UiO-66(Hf) metal-organic framework for the synthesis of quinolines via Friedl?nder condensation

A hydrazine functionalized Hf-UiO-66 metal-organic framework (MOF) (called 1) was prepared using the traditional solvothermal method and it was characterized completely. The material showed high chemical stability in various solvent systems. The activated material (called 1′) was successfully used as a solid heterogeneous catalyst for the synthesis of quinolone scaffolds in a modified Friedl?nder synthesis. The catalyst was able to produce 95% yield of the product 3-acetyl-2,4-dimethylquinoline via Friedl?nder condensation of 2-aminoacetophenone and acetylacetone as starting materials at 100 °C. It also exhibited a broad substrate scope in this catalytic reaction. Various control experiments were carried out with respect to the activity of the presented catalyst which clearly indicated its active role. The stability and recyclability of the catalyst were also examined. A series of control experiments for this catalysis have shown that the Lewis acidic metal nodes and Br?nsted acidic -NHNH2 functional groups of linker play active roles in the catalysis.

Quinoline- and 1,8-naphthyridine-3-carboxylic acids using a self-catalyzed Friedl?nder approach

One-step syntheses of 2-alkyl- and 2,4-dialkyl-substituted quinoline-3-carboxylic acids and 1,8-naphthyridine-3-carboxylic acids are reported using a catalyst-free Friedl?nder reaction. The reaction is carried out in one step by simple heating of 2-aminobenzaldehyde, 2-amino-5-chlorobenzaldehyde, 2-aminonicotinaldehyde, or 2-aminoacetophenone with a β-ketoester in toluene or xylene for 24 h. Under these conditions, the carboxylic acid product is isolated directly from the reaction mixture without need for further purification. The observation that the reaction starts slowly and accelerates as it proceeds suggests that the transformation is self-catalyzed. This hypothesis is also supported by the finding that attempts to extend the current reaction to diketones, which cannot hydrolyze to an acid, were generally unsuccessful.

Microwave-assisted Friedl?nder synthesis of polysubstituted quinolines based on poly(ethylene glycol) bound acetoacetate

Polysubstituted quinolines were efficiently prepared on the soluble polyethylene glycol (PEG) by microwave irradiation Friedl?nder condensation of PEG bound acetoacetate with 2-aminoarylketones promoted by catalytic amount of polyphosphoric acid, and subsequently cleavage from the PEG withMeONa in MeOH. The polymer-supported synthesis provided the target compounds in excellent yield and purity with a facile work-up procedure.

NAD(P)+-NAD(P)H MODELS. 57. STEROCHEMISTRY IN (NET) HYDRIDE TRANSFER FROM AND TO NAD(P)+-NAD(P)H MODELS: CHIRALITY SINK

NAD(P)H/NAD(P)+ and related compounds have intrinsic chirality against the axis along the C3-Ccarbonyl single bond.A model compound which has a stable conformation with respect to this chirality was synthesized and the conformational relationship between the carbonyl dipole and the reacting hydrogen was studied.It has been concluded that there is a relationship between conformations of these groups both in reduction and in oxidation provided the substrate is a neutral species.The result is discussed in relation with the hypothesis proposed previously on the basis of quantum chemical calculations.