PRMAQUINE

PRMAQUINE




Brand Name: SN 13272.

Primaquine is a quinolinic N antimalarial which retains the 6- methoxyl group of the quinine model.



The basic side chain is attached at C-8 in place of C-4 position. The starting compound for the preparation of primaquine is 4-amino-3-nitroanisole, which is prepared from anisole by normal synthetic reactions. A Skraup reaction converts this compound into 6-methoxy-8-nitroquinoline by heating a mixture of the aniline, glycerol, sulphuric acid and an oxidizing agent (usually nitrobenzene or arsenic acid). 


The reduction of 6-methoxy-8-nitroquinolineyields 8-amino-6-methoxyquinoline.

The side chain is introduced by using the Gabriel primary amine synthesis. 4-Bromo-1-phthalimidopentane is prepared by reacting 1,4-dibromopentane and phthalimide which is condensed with the aminoquinoline. The phthalyl group is then removed either by direct hydrolysis or by forming an intermediate compound with hydrazine which is decomposed by dilute acids:
Primaquine is a viscous liquid, b.p. 175-179; soluble in ether; protected from light. Its diphosphate salt is used as antimalarial drug.



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