反应详情

A mixture of the above-8-aminoquinoline (VII 3.0 g, 8.6 mmol), 4-iodo-1-phthalimidopentane (IPP) 3.0 g, 8.7 mmol), triethylamine (TEA) (1.2 mL) and 2-ethoxyethanol (6 mL) was heated at 105° for 2.5 hours, after which time an additional quantity of IPP (3 g) and TEA (1.2 mL) was added. After an additional 4 hours at 105°, the mixture was cooled and dissolved in chloroform. The chloroform solution was washed with 10% aqueous potassium hydroxide and with water, dried and concentrated to dryness. The residue was dissolved in ether and excess ethereal HCL was added. The ether was decanted and the gum was triturated in fresh ether (×2). The gum was then shaken with ether and 10% aqueous potassium carbonate. The ether was removed and the residue was heated in ethanol (15 mL). The mixture was cooled and the solid was filtered to give 1.65 g of the title compound. The filtrate was concentrated to dryness and the residue was triturated in hot ligroin (bp 60°-80°, 50 mL). The ligroin was decanted from a little insoluble gum and concentrated to dryness to afford 1.5 g of additional crude product. The combined crops were crystallized from ethanol (75 mL) to give 2.75 g (57%) of pure title compound, mp 143°-145°.

1. temperaturewas heated at 105° for 2.5 hours
2. temperaturethe mixture was cooled
3. washThe chloroform solution was washed with 10% aqueous potassium hydroxide and with water
4. customdried
5. concentrationconcentrated to dryness
6. dissolutionThe residue was dissolved in ether
7. additionexcess ethereal HCL was added
8. customThe ether was decanted
9. customthe gum was triturated in fresh ether (×2)
10. customThe ether was removed
11. temperaturethe residue was heated in ethanol (15 mL)
12. temperatureThe mixture was cooled
13. filtrationthe solid was filtered