Quinolines, 4-diethylamino-, synthesis

Some applications of the described reactions include the preparation of chloroquine, an important anti-malarial, which is made by reacting 4,7-dichloroquinoline with 4-diethylamino-l-methylbutylamine at 180 °C. 7-Chloro-4-hydroxyquinoline, a precursor of 4,7-dichloroquinoline, was routinely prepared by heating 3-chloroaniline with the ethyl ester of formylacetic acid, through the Conrad-Limpach quinoline synthesis. ... 

Table 2 shows the effect of each purine inhibitor on incorporation of ( H) hypoxanthine into nucleic acids (acid-insoluble PCA fraction) of malaria infected erythrocytes. Two clinically proven antimalarial drugs, chloroquine (7-chloro-4-(4 -diethylamino-methyl-butylamino)-quinoline) and mefloquine (a-(2-piperidyl)-2, 8-bis (trifluoro-methyl)-4-quinolinemethenol hydrochloride), were included for comparison. Hadacidin, bredinin and mycophenolic acid all produced significant (p <. 005) decreases in nucleic acid synthesis by PRBC as measured by incorporation of ( H) hypoxanthine. Alanosine had no demonstrable effect. 

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