反应详情

An aqueous solution (200 mL) of potassium carbonate (55.3 g, 400 mmol) and sodium dithionate (62.7 g, 360 mmol) was added dropwise over 30 minutes to a mixture of N-allyl-2-chloro-3-nitroquinolin-4-amine (21.0 g, 79.9 mmol) and ethyl viologen dibromide (1.80 g, 4.80 mmol) in dichloromethane (320 mL) and water (40 mL) under a nitrogen atmosphere. The dark blue-green mixture was stirred rapidly and was heated at reflux overnight. The mixture was transferred to a separatory funnel and the layers were separated. The aqueous layer was extracted with dichloromethane. The combined organic layers were filtered through CELITE filter agent, dried over magnesium sulfate, filtered, and concentrated to a dark oil. The crude product was purified by suction filter chromatography (silica gel, gradient elution from 3:1 to 1:3 hexanes/ethyl acetate, then 4:1 dichloromethane/ethyl acetate) to afford pure product N4-allyl-2-chloroquinoline-3,4-diamine (12.06 g) along with some impure product (3.10 g).

1. temperaturewas heated
2. temperatureat reflux overnight
3. customThe mixture was transferred to a separatory funnel
4. customthe layers were separated
5. extractionThe aqueous layer was extracted with dichloromethane
6. filtrationThe combined organic layers were filtered through CELITE
7. filtrationfilter agent
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated to a dark oil
11. customThe crude product was purified by suction
12. filtrationfilter chromatography (
13. washsilica gel, gradient elution from 3:1 to 1:3 hexanes/ethyl acetate