4363-93-3

Usage

Uses

Used in Pharmaceutical Industry:
4-Quinolinecarboxaldehyde is used as an intermediate in the synthesis of lepidylamines, which are compounds with potential pharmaceutical applications.
Used in Antimicrobial Applications:
4-Quinolinecarboxaldehyde is used as an antimicrobial agent for its activity against human intestinal bacteria such as Clostridium perfringens, which can be beneficial in the treatment and prevention of certain infections.

Synthesis Reference(s)

The Journal of Organic Chemistry, 35, p. 841, 1970 DOI: 10.1021/jo00828a074

InChI:InChI=1/C10H7NO/c12-7-8-5-6-11-10-4-2-1-3-9(8)10/h1-7H

Upstream product

• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 110-88-3 1,3,5-Trioxan 
• 91-22-5 quinoline 
• 2591-98-2 indole-3-acetaldehyde 
• 5450-80-6 1-[4]quinolylmethyl-pyridinium; iodide 
• 611-35-8 4-chloroquinoline 
• 20461-86-3 2,2-diethoxy acetic acid 
• 79-43-6 dichloro-acetic acid 
• 6281-32-9 4-quinolylmethanol 
• 1912-33-0 Indole-3-acetic acid methyl ester 
• 87-51-4 indole-3-acetic acid 
• 7446-08-4 selenium(IV) oxide 
• 108-88-3 toluene 
• 123-91-1 1,4-dioxane 

Downstream Products

• 486-74-8 4-quinolinic acid 
• 55908-34-4 1-Quinolin-4-yl-ethanol 
• 109805-22-3 3c-[4]quinolyl-2-(3,4-dimethoxy-phenyl)-acrylonitrile 
• 141265-66-9 4-[4]quinolylmethylenamino-phenol 
• 53274-27-4 diethyl 1,4-dihydro-2,6-dimethyl-4-(4-quinolinyl)pyridine-3,5-dicarboxylate 
• 109558-06-7 benzoyloxy-[4]quinolyl-acetonitrile 
• 680590-98-1 ethyl-[4]quinolylmethyl-amine 
• 1477-60-7 4-quinolinecarboxaldehyde thiosemicarbazone 

Relevant academic research and scientific papers

Synthetic approaches to Cinchona alkaloids: The C-8/C-9 disconnection strategy

When conducted in DMSO, the Hünig's base-promoted condensation of 3-quinuclidinone with quinoline-4-carboxaldehyde gave an equimolar mixture of epimeric aldols 8 with an excellent yield.

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.

Iodine-imine Synergistic Promoted Povarov-Type Multicomponent Reaction for the Synthesis of 2,2′-Biquinolines and Their Application to a Copper/Ligand Catalytic System

An efficient iodine-imine synergistic promoted Povarov-type multicomponent reaction was reported for the synthesis of a practical 2,2′-biquinoline scaffold. The tandem annulation has reconciled iodination, Kornblum oxidation, and Povarov aromatization, where the methyl group of the methyl azaarenes represents uniquely reactive input in the Povarov reaction. This method has broad substrate scope and mild conditions. Furthermore, these 2,2′-biquinoline derivatives had been directly used as bidentate ligands in metal-catalyzed reactions.

Iron(III) Nitrate/TEMPO-Catalyzed Aerobic Alcohol Oxidation: Distinguishing between Serial versus Integrated Redox Cooperativity

Aerobic alcohol oxidations catalyzed by transition metal salts and aminoxyls are prominent examples of cooperative catalysis. Cu/aminoxyl catalysts have been studied previously and feature "integrated cooperativity", in which CuII and the aminoxyl participate together to mediate alcohol oxidation. Here we investigate a complementary Fe/aminoxyl catalyst system and provide evidence for "serial cooperativity", involving a redox cascade wherein the alcohol is oxidized by an in situ-generated oxoammonium species, which is directly detected in the catalytic reaction mixture by cyclic step chronoamperometry. The mechanistic difference between the Cu- and Fe-based catalysts arises from the use iron(III) nitrate, which initiates a NOx-based redox cycle for oxidation of aminoxyl/hydroxylamine to oxoammonium. The different mechanisms for the Cu- and Fe-based catalyst systems are manifested in different alcohol oxidation chemoselectivity and functional group compatibility.

Hydroxymethylation of quinolinesviairon promoted oxidative C-H functionalization: synthesis of arsindoline-A and its derivatives

Herein, we report a mild and efficient hydroxymethylation of quinolinesviaan iron promoted cross-dehydrogenative coupling reaction under external acid free conditions. Various hydroxyalkyl substituted quinolines were achieved in excellent yields with well tolerated functional groups. Importantly, a few of the hydroxylmethylated quinolines were further transformed into respective aldehydes, and were successfully utilized for the synthesis of alkaloid arsindoline-A and its derivatives.

Facile synthesis of 1,3,4-oxadiazoles via iodine promoted oxidative annulation of methyl-azaheteroarenes and hydrazides

An oxidative sp3 C–H bond of methyl-azaheteroarenes protocol was reported for the synthesis of 1,3,4-oxadiazoles via [4 + 1] annulation with hydrazides. This protocol enables 1,3,4-oxadiazole and quinoline linked diheterocycles via selective oxidation of sp3 C–H bond of methyl-azaheteroarenes in the presence of I2-DMSO. The reaction has a broad substrate scope and good functional group tolerance for methyl-azaheteroarenes and hydrazides.

Metal- and radical-free aerobic oxidation of heteroaromatic methanes: An efficient synthesis of heteroaromatic aldehydes

A metal-free and radical-free synthesis of heteroaromatic aldehydes was developed through aerobic oxidation of methyl groups in an I2/DMSO/O2 catalytic system. Under the reaction conditions, various functional groups such as methoxy, aldehyde, ester, nitro, amide, and halo (F, Cl, Br) groups were well tolerated. The bioactive compounds like chlorchinaldin derivative and papaverine were also oxidized to the corresponding aldehydes and ketones. This reaction provided an efficient method for preparing the valuable heteroaromatic aldehydes.

Transition-Metal-Free Oxidation of Benzylic C-H Bonds of Six-Membered N-Heteroaromatic Compounds

A novel oxidation of benzylic C-H bonds for the synthesis of diverse six-membered N-heteroaromatic aldehydes and ketones has been developed. The obvious advantages of this approach are the simple operation, mild reaction conditions, and without use of toxic reagent and transition metal. The present method should provide a useful access for the synthesis and modification of N-heterocycles.

Visible-Light-Promoted Nickel- and Organic-Dye-Cocatalyzed Formylation Reaction of Aryl Halides and Triflates and Vinyl Bromides with Diethoxyacetic Acid as a Formyl Equivalent

A simple formylation reaction of aryl halides, aryl triflates, and vinyl bromides under synergistic nickel- and organic-dye-mediated photoredox catalysis is reported. Distinct from widely used palladium-catalyzed formylation processes, this reaction proceeds by a two-step mechanistic sequence involving initial in situ generation of the diethoxymethyl radical from diethoxyacetic acid by a 4CzIPN-mediated photoredox reaction. The formyl-radical equivalent then undergoes nickel-catalyzed substitution reactions with aryl halides and triflates and vinyl bromides to form the corresponding aldehyde products. Significantly, besides aryl bromides, less reactive aryl chlorides and triflates and vinyl halides serve as effective substrates for this process. Since the mild conditions involved in this reaction tolerate a plethora of functional groups, the process can be applied to the efficient preparation of diverse aromatic aldehydes.

Copper-Catalyzed Aerobic Oxidation of Azinylmethanes for Access to Trifluoromethylazinylols

A copper-catalyzed oxygenation of methylazaarenes was found to occur in the absence of both ligand and additive, and has been successfully employed for the synthesis of trifluoromethylazinylketols. This synthetic strategy incorporates aerobic oxidation and a trifluoromethylation in one-pot and provides a novel method for the trifluoromethylation of aliphatic C-H bond.