6- Methoxy-5-bromo-8-nitroquinoline

By the same procedure the submitters have prepared 6-ethoxy-8-nitroquinoline in 70% yield, 8-methoxy-6-nitroquino-line in 68% yield, 6-chloro-8-nitroquinoline in 75% yield, and 6-methoxy-5-bromo-8-nitroquinoline in 69% yield from the properly substituted aromatic amines. 

Primaquine Primaquine, 8-[(4-amino-l-methylbutyryl)amino]-6-methoxyquinoline (37.1.2.4), is made from 6-methoxy-8-nitroquinoline (37.1.2.1), which is synthesized in a Skraup reaction from 4-methoxy-2-nitroaniline and glycerol in the presence of sulfuric acid. The nitro group in this compound is reduced to make 6-methoxy-8-aminoquinoline (37.1.2.2). Alkylating the amino group with 4-bromo-l-phthalimidopentane gives 8-[(4-phthalimido-l-methylbutyryl)amino]-6-methoxyquinoline (37.1.2.3), the hydrazi-nolysis of which removes the phthalimide protection, giving primaqnine [28,29]. 

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