From chloroquine to nalidixic acid...

nalidixic acid

N

HN

Cl

N

CH

3

CH

3

chloroquine

1939

1958

1962

N

C

O

C

2

H

5

O

-

O

Cl

N

N

C

O

O

-

H

3

C

O

C

2

H

5

7-chloroquinoline

(synthesis intermediate

found to display

antibacterial activity)

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