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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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Chloroquine (CQ) then becomes protonated (to CQ 2+), as the digestive vacuole is known to be acidic (pH 4.7); chloroquine then cannot leave by diffusion. Chloroquine caps hemozoin molecules to prevent further biocrystallization of heme, thus leading to heme buildup.
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
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