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Usage

Uses

Used in Pharmaceutical and Chemical Industries:
8-Quinolinecarboxylic acid is used as a key intermediate in the synthesis of novel oxorhenium(V) complexes incorporating quinoline and isoquinoline carboxylic acid derivatives. These complexes have potential applications in medicinal chemistry and catalysis.
Used in Asymmetric Catalysis:
8-Quinolinecarboxylic acid is used as a precursor for the synthesis of chiral 1,2,3,4-tetrahydroquinolinyl-oxazoline compounds. These compounds serve as ligands for Ru-catalyzed asymmetric transfer hydrogenation of ketones, a crucial reaction in the synthesis of enantiomerically pure pharmaceuticals and agrochemicals.
Used in Organic Synthesis:
8-Quinolinecarboxylic acid is also used in the synthesis of chiral quinolinyl-oxazoline compounds, which act as ligands for Cu(II) catalyzed asymmetric cyclopropanation. This reaction is an important method for the formation of cyclopropane rings in organic molecules, which are found in various biologically active compounds and materials.

Purification Methods

Crystallise the acid from water, aqueous EtOH, EtOH or *C6H6. The ethyl ester has m 45o and b 194-197o/13mm. [Beilstein 22 H 81, 22 III/IV 1200, 22/3 V 217.]

InChI:InChI=1/C10H7NO2/c12-10(13)8-5-1-3-7-4-2-6-11-9(7)8/h1-6H,(H,12,13)/p-1

Upstream product

• 611-32-5 8-methylquinoline 
• 19655-56-2 8-ethylquinoline 
• 35509-27-4 quinoline-8-carbonitrile 
• 118-92-3 anthranilic acid 
• 56-81-5 glycerol 
• 552-16-9 ortho-nitrobenzoic acid 
• 7496-46-0 8-bromomethyl-quinoline 
• 94127-04-5 8-chloromethyl-quinoline 
• 215606-70-5 8-iodomethylquinoline 
• 72804-93-4 8-ethyl-2-methylquinoline 
• 72804-91-2 8-ethylquinoline-2-carbaldehyde 
• 77739-84-5 8-ethyl-quinoline-2-carboxylic acid 
• 578-54-1 ortho-ethylaniline 
• 16567-18-3 8-bromoquinoline 

Downstream Products

• 40245-26-9 quinoline-8-carboxylic acid methyl ester 
• 25635-22-7 quinoline-8-carboxylic acid ethylester 
• 107456-13-3 quinoline-8-carboxylic acid butyl ester 
• 34849-19-9 1,2,3,4-tetrahydro-8-quinolinecarboxylic acid 
• 100517-41-7 quinoline-8-carbonyl chloride 
• 89-00-9 Pyridine-2,3-dicarboxylic acid 
• 899431-52-8 quinoline-8-carboxylic acid benzylamide 
• 220628-89-7 (1'S)-N-(1'-phenyl-2'-hydroxyethyl)-8-quinolinecarboxamide 
• 220628-87-5 (1'S)-N-(1'-benzyl-2'-hydroxyethyl)-8-quinolinecarboxamide 
• 426823-07-6 N-[(1S)-1-phenyl-2-hydroxyethyl]-(1,2,3,4-tetrahydroquinolin-8-yl)-carboxamide 
• 426823-03-2 N-[(1S)-1-benzyl-2-hydroxyethyl]-(1,2,3,4-tetrahydroquinolin-8-yl)-carboxamide 
• 22765-51-1 Chinolin-8-carbonsaeureanilid 
• 220628-98-8 (S)-8-<4,5-dihydro-4-(1-methylethyl)oxazol-2-yl>quinoline 

Relevant academic research and scientific papers

Synthesis derivatives of 2-amino-4-quinolones from 1,2,3,4- tetrahydroquinoline-8-carboxylic acids

A simple and efficient method is developed. Novel 2-amino-4-quinolone derivatives are synthesized. The products that have several functional groups for possible future modifications are described.

Method for preparing 8-quinoline carboxylic acid and derivatives of 8-quinoline carboxylic acid

The invention discloses a method for preparing 8-quinoline carboxylic acid and derivatives thereof, which comprises the following steps: by using a compound I as a raw material, reacting with an oxidant at the temperature of 50-150 DEG C under normal pressure in a solvent under the action of a Cu-Co-X ternary composite catalyst to obtain a compound II; according to the method, the efficient Cu-Co-X ternary composite catalyst is adopted, the reaction is carried out at the temperature of 50-150 DEG C under normal pressure, the reaction condition is mild, the oxidation yield is remarkably increased, near-zero emission of three wastes is realized, the pollution problem is effectively solved, and the production cost is greatly reduced.

Redox couple involving NOx in aerobic Pd-catalyzed oxidation of sp3-C-H bonds: Direct Evidence for Pd-NO3-/NO2- interactions involved in oxidation and reductive elimination

NaNO3 is used in oxidative Pd-catalyzed processes as a complementary co-catalyst to common oxidants, e.g., CuII salts, in C-H bond activation and Wacker oxidation processes. NaNO3 and NaNO2 (with air or O2

Development and Mechanistic Study of Quinoline-Directed Acyl C-O Bond Activation and Alkene Oxyacylation Reactions

The intramolecular addition of both an alkoxy and acyl substituent across an alkene, oxyacylation of alkenes, using rhodium catalyzed C-O bond activation of an 8-quinolinyl ester is described. Our unsuccessful attempts at intramolecular carboacylation of ketones via C-C bond activation ultimately informed our choice to pursue and develop the intramolecular oxyacylation of alkenes via quinoline-directed C-O bond activation. We provide a full account of our catalyst discovery, substrate scope, and mechanistic experiments for quinoline-directed alkene oxyacylation.

Insertion of an Alkene into an ester: Intramolecular oxyacylation reaction of alkenes through acyl C-O bond activation

Atom economy and esters: compatible now! The first catalytic insertion of a C-C bond into an acyl C-O bond was achieved using rhodium catalysts (see scheme). The products are β-alkoxy ketones with a fully substituted carbon center. Quinoline chelating groups were employed to stabilize the Rh-alkoxide intermediate.

Remarkable effect of nitrogen dioxide for N-hydroxyphthalimide-catalyzed aerobic oxidation of methylquinolines

Aerobic oxidation of methylquinolines was successfully achieved by the use of N-hydroxyphthalimide/Co(OAc)2/Mn(OAc)2 as catalyst in the presence of a small amount of nitrogen dioxide as an initiator.

Biocatalytic oxidation of 2-methylquinoxaline to 2-quinoxalinecarboxylic acid

A microbial process using the fungus Absidia repens ATCC 14849 is described for the oxidation of 2-methylquinoxaline to 2-quinoxalinecarboxylic acid. A campaign consisting of three 14000-L runs produced 20.5 kg of the acid with a 28% overall yield. The bioconversion gave a lower yield compared with a three step chemical synthesis (35%), but was carried out in one pot, and avoided safety issues with a di-N-oxide intermediate. Although successfully scaled to produce kilograms of 2-quinoxalinecarboxylic acid for synthesis of a drug candidate, the A. repens bioconversion is unsuitable for further scale-up due to low product concentration (～1 g/L). A second microbial process using Pseudomonas putida ATCC 33015 is also described for the oxidation of 2-methylquinoxaline. The P. putida bioconversion gave an 86% in situ yield at 8-L scale and yielded a product concentration approximately 10-fold greater than that of the A. repens bioconversion.

ALKALOIDS OF Nitraria komarovii. IV. TOTAL SYNTHESIS OF KOMAROVINE AND KOMAROVIDINE

Two alkaloids of a new type - komarovine and komarovidine - have been isolated from the epigeal part of the Nitraria komarovii.Their structures - 3-(quinolin-8'-yl)-β-carboline and 3-(quinolin-8'-yl)-5,6-dihydro-β-carboline, respectively - have been established by synthesis.