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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 .
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[1] [4] Chloroquine is a member of the drug class 4-aminoquinoline. [1] As an antimalarial, it works against the asexual form of the malaria parasite in the stage of its life cycle within the red blood cell. [1] How it works in rheumatoid arthritis and lupus erythematosus is unclear. [1] Chloroquine was discovered in 1934 by Hans Andersag.
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A 6 electron cyclization reaction with the loss of another ethanol molecule forms a quinoline (ethyl 4-oxo-4,4a-dihydroquinoline-3-carboxylate). The enol form can be represented from the keto form through keto-enol tautomerism. Protonation of the nitrogen forms ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylate. Mechanism for the Gould-Jacobs reaction
[3] [4] Although all risk cannot be excluded, it remains a treatment for rheumatic disease during pregnancy. [5] Hydroxychloroquine is in the antimalarial and 4-aminoquinoline families of medication. [3] Hydroxychloroquine was approved for medical use in the United States in 1955. [3] It is on the World Health Organization's List of Essential ...