86-59-9 Usage
Description
8-Quinolinecarboxylic acid is an organic compound belonging to the quinoline carboxylic acid family, characterized by its fused pyridine and benzene rings with a carboxylic acid functional group at the 8th position. It serves as a versatile building block in the synthesis of various complex organic molecules and metal complexes.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 86-59-9 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 6 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 86-59:
(4*8)+(3*6)+(2*5)+(1*9)=69
69 % 10 = 9
So 86-59-9 is a valid CAS Registry Number.
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
86-59-9Relevant articles and documents
Synthesis derivatives of 2-amino-4-quinolones from 1,2,3,4- tetrahydroquinoline-8-carboxylic acids
Listunov, Dimitriy,Popov, Kirill,Tkachuk, Tetyana,Volovenko, Yulian
, p. 660 - 662 (2013)
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.
Development and Mechanistic Study of Quinoline-Directed Acyl C-O Bond Activation and Alkene Oxyacylation Reactions
Hoang, Giang T.,Walsh, Dylan J.,McGarry, Kathryn A.,Anderson, Constance B.,Douglas, Christopher J.
, p. 2972 - 2983 (2017/03/23)
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
Hoang, Giang T.,Reddy, Venkata Jaganmohan,Nguyen, Huy H. K.,Douglas, Christopher J.
supporting information; experimental part, p. 1882 - 1884 (2011/04/16)
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.
