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2-Chloroquinoline is an organic compound with the formula ClC 9 H 6 N. It is one of several isomeric chloro derivatives of the bicyclic heterocycle called quinoline . A white solid, 2-chloroquinoline can be prepared from vinylaniline and phosgene. [ 1 ]
Oxidation of quinoline affords quinolinic acid (pyridine-2,3-dicarboxylic acid), a precursor to the herbicide sold under the name "Assert". [ 8 ] The reduction of quinoline with sodium borohydride in the presence of acetic acid is known to produce Kairoline A . [ 15 ] (
The systematic IUPAC name is not always the preferred IUPAC name, for example, lactic acid is a common, and also the preferred, name for what systematic rules call 2-hydroxypropanoic acid. This list is ordered by the number of carbon atoms in a carboxylic acid.
Ozonolysis of oleic acid is an important route to azelaic acid. The coproduct is nonanoic acid: [15] H 17 C 8 CH=CHC 7 H 14 CO 2 H + 4"O" → HO 2 CC 7 H 14 CO 2 H + H 17 C 8 CO 2 H. Esters of azelaic acid find applications in lubrication and plasticizers. Neutralizing oleic acid with ethanolamines gives the protic ionic liquid monoethanolamine ...
4,7-Dichloroquinoline was first reported in a patent filed by IG Farben in 1937. [2] However, its synthesis was not investigated in detail until chloroquine was developed as an antimalarial drug. [ 3 ] : 130–132 A route to the intermediate starting from 3-chloroaniline was developed by chemists at Winthrop Chemical Co .
The mixture produced a polyphosphoric ester (PPE) catalyst that proved to be more effective as the dehydrating agent than concentrated sulfuric acid (H 2 SO 4), which is commonly used in the Combes quinoline synthesis. Using the modified Combes synthesis, two possible regioisomers were found: 2-CF 3 - and 4-CF 3-quinolines.
After a cyclization at the benzene ring and two proton shifts, the quinoline-4-carboxylic acid (4) is formed by water elimination: [4] Reaktionsmechanismus-Vorschlag (1) der Doebner-Reaktion An alternative mechanism is based on the aniline and the aldehyde forming at first the Schiff base upon water elimination.
The reaction of isatin with a base such as potassium hydroxide hydrolyses the amide bond to give the keto-acid 2. This intermediate can be isolated, but is typically not. A ketone (or aldehyde) will react with the aniline to give the imine (3) and the enamine (4). The enamine will cyclize and dehydrate to give the desired quinoline (5).