Synthesis of chloroquine Synthesis of primaquine Synthesis of quinacrine Chloroquine is prepared from 2-nitro aniline Primaquine is prepared from 1,4-dibromopentane Quinacrine is prepared from 2,4-dichloro benzoic acid

1. Medicinal Chemistry-III
Antimalarial agents 3
Department of Pharmacy, Indira Gandhi National Tribal
University, Lalpur, Amarkantak (M.P.)
Dr. Akhilesh Tiwari
Assistant Professor
Department of Pharmacy,
IGNTU, Amarkantak

2. CONTENTS
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• Synthesis of chloroquine
• Synthesis of primaquine
• Synthesis of quinacrine

3. At the end of this lecture, student will be able to
• Explain the synthetic route for the synthesis of chloriquine
• Explain the synthetic route for the synthesis of primaquine
• Explain the synthetic route for the synthesis of quinacrine
LEARNING OBJECTIVES
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4. SYNTHESIS OF CHLOROQUINE
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• It is prepared by adopting the following four steps viz.,
• (a) Preparation of 4, 7-Dichloroquinoline (i.e., the nucleus)
• (b) Preparation of 2-amino-5-diethyl amino pentane,
diethylamino-4-amino pentane (i.e.,the side chain).
or 1-
• (c) Condensation of ‘a’ and ‘b’.
• (d) Addition of concentrated phosphoric acid to a hot ethanolic
solution of the condensed product.

5. A) PREP. OF NUCLEUS
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6. B) PREP. OF SIDE CHAIN
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7. C) CONDENSATION OF A AND B
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8. D) PREP. OF PHOSPHATE SALT
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9. SYNTHESIS OF CHLOROQUINE
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10. SYNTHESIS OF CHLOROQUINE CONTD…
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11. SYNTHESIS OF CHLOROQUINE CONTD…
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12. SYNTHESIS OF PAMAQUINE
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• Synthesis of the nucleus

13. SYNTHESIS OF PAMAQUINE
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• Condensation of the side chain and nucleus
8 Amino 6 methoxy quiniline
2 chlorodiethyl amino pentane

14. SYNTHESIS OF QUINACRINE
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• Synthesis of the nucleus
• Condensation with the side chain

15. SUMMARY
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• Chloroquine is prepared from 2-nitro aniline
• Primaquine is prepared from 1,4-dibromopentane
• Quinacrine is prepared from 2,4-dichloro benzoic acid