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4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

hydrazine

acetic acid

→

4-hydrazino-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

용매

water

water

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후처리

1. 1
   온도The mixture heated rapidly
2. 2
   온도to reflux
3. 3
   workup.DISSOLUTIONThe solid dissolved with
4. 4
   온도a vigorous heat of reaction
5. 5
   기타a precipitate formed as the reaction mixture
6. 6
   온도refluxed
7. 7
   기타The precipitate was isolated by filtration
8. 8
   여과The solution was filtered
9. 9
   기타to remove traces of undissolved solid
10. 10
    workup.ADDITIONThe filtrate was made basic by the addition of ammonium hydroxide
11. 11
    기타The resulting precipitate was isolated by filtration
12. 12
    세척washed with water
13. 13
    기타then dried
14. 14
    기타to provide 8.0 g of crude product as a white solid
15. 15
    기타A sample of this material was recrystallized from methanol

실험 절차

4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline (10.0 g, 0.0385 moles, U.S. Pat. No. 4,689,338 Example 77) was added to hydrazine (30 mL). The mixture heated rapidly to reflux. The solid dissolved with a vigorous heat of reaction then a precipitate formed as the reaction mixture refluxed. The reaction mixture was diluted with water. The precipitate was isolated by filtration then suspended in water (100 mL). The solid was brought into solution by the addition of acetic acid. The solution was filtered to remove traces of undissolved solid. The filtrate was made basic by the addition of ammonium hydroxide. The resulting precipitate was isolated by filtration, washed with water then dried to provide 8.0 g of crude product as a white solid. A sample of this material was recrystallized from methanol to provide 4-hydrazino-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline, m.p. 202-205° C. Analysis: Calculated for C14H17N5 : % C, 65.86; % H, 6.71; % N, 27.43; Found: % C, 65.20; % H, 6.6; % N, 27.5.

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