Hydrogen Bromide → 5-[p-Chlorophenoxy]-6-methoxy-8-[4-phthalimido-1-methylbutylamino]quinoline

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Reaction Steps

A stirred mixture of 8-amino-5-(4-chlorophenoxy)- 6-methoxyquinoline (6.2 g, 0.02 mole), 4-bromo-1-phthalimidopentane (6.0 g, 0.02 mole), and triethylamine (2.0 g, 0.02 mole) was heated at 130°-135° for 12 hr. The cooled mixture was extractively treated with arm acetone (50 ml), cooled, and triethylamine hydrobromide collected (3.2 g, 89%). The filtrates were concentrated to dryness, and the residues taken up in chloroform, then treated with 48% hydrobromic acid. The chloroform layer was dried and concentrated, then absolute ether added to precipitate the hydrobromide of the desired compound (8.2 g, 70% yield). As obtained, the hydrobromide melted 194°-198°; following crystallization from ethanol, mp 214°-215°. It analyzed as a monohydrate. The base was liberated as a crystalline solid of mp 75°-77°.

Provenance & Evidence