Antimalarial Drugs.pptx
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1) The document discusses the synthesis of the antimalarial drug chloroquine. 2) It describes the chemical reactions used to synthesize an intermediate component called 4,7-dichloroquinoline from 3-chloroaniline and other reactants. 3) The final synthesis of chloroquine involves reacting 4,7-dichloroquinoline with 4-diethylamino-1-methylbutylamine at high temperature.
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Antimalarial Drugs.pptx
- 1. Antimalarial Drugs By Dr. Nidhi Gupta M. M. (Deemed to be University), Mullana, Ambala
- 46. Chloroquine synthesis contd. • Reacting 3-chloroaniline with ethoxymethylenmalonic ester to make (3-choroanilino)-methylenemalonic ester (37.1.1.4), which then undergoes high-temperature heterocyclization to make the ethyl ester of 7-chloro-4-hydroxyquinolin-3-carboxylic acid. • Hydrolyzing this with sodium hydroxide gives 7-chloro-4- hydroxyquinolin-3-decarboxylic acid, which when heated at 250–270 C is decarboxylated, forming 7-chloro-4-hydroxyquinoline. • Treating this with phosphorus oxychloride gives one of the desired components for synthesis of chloroquine – 4,7-dichloroquinoline.
- 47. Chloroquine synthesis contd. 7-chloro-4-(4-diethylamino-1-methylbutylamino)-quinoline is made by reacting 4,7-dichloroquinoline with 4-diethylamino-1-methylbutylamine at 180 °C.