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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 ] (
Quinaldine or 2-methylquinoline is an organic compound with the formula CH 3 C 9 H 6 N. It is one of the methyl derivatives of the heterocyclic compound quinoline. It is bioactive and is used in the preparation of various dyes. It is a colorless oil but commercial samples can appear colored. [1]
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 .
4-Quinolone is an organic compound derived from quinoline. It and 2-quinolone are the two most important parent (meaning simplified) quinolones. 4-Quinolone exists in equilibrium with a minor tautomer, 4-hydroxyquinoline (CAS#611-36-9).
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.
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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).
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