反应 #1379891

反应方程式

5-aminoquinoline

acetaldehyde

4-thiocresol

→

yellow solid

收率 62.7%

ethylquinolin-5-yl-amine

收率 62.7%

溶剂

ethanol

反应条件

后处理

1. 1
   温度at reflux for 4 h
2. 2
   其他The reaction mixture was evaporated under reduced pressure
3. 3
   workup.DISSOLUTIONthe residue dissolved in ethanol (100 ml)
4. 4
   workup.ADDITIONSodium borohydride (10 g) was then added to the reaction mixture in portions
5. 5
   温度maintaining the temperature below 5° C
6. 6
   workup.STIRRINGThis reaction mixture was stirred
7. 7
   温度at reflux for 2 h
8. 8
   workup.ADDITIONWater (40 ml) was then added
9. 9
   workup.STIRRINGthe mixture was stirred for a further 25 min
10. 10
    温度at reflux
11. 11
    萃取the product was extracted with dichloromethane (4×100 ml)
12. 12
    洗涤washed with water (250 ml)
13. 13
    干燥before being dried over MgSO4
14. 14
    其他The solvent was then removed under reduced pressure
15. 15
    其他the residue was purified by column chromatography on silica gel eluting with ethyl acetate in hexane
16. 16
    其他The solvent in the eluent was evaporated

实验过程

A mixture of 5-aminoquinoline (7.2 g, 0.05 mol), acetaldehyde (2.6 g, 0.06 mol) and 4-thiocresol (6.8 g, 0.055 mol) in ethanol (100 ml) was stirred at reflux for 4 h. The reaction mixture was evaporated under reduced pressure and the residue dissolved in ethanol (100 ml). Sodium borohydride (10 g) was then added to the reaction mixture in portions maintaining the temperature below 5° C. This reaction mixture was stirred at reflux for 2 h and cooled to room temperature. Water (40 ml) was then added and the mixture was stirred for a further 25 min at reflux. The pH of the mixture was then adjusted to pH8 with 2N NaOH and the product was extracted with dichloromethane (4×100 ml). The dichloromethane extracts were combined and washed with water (250 ml) before being dried over MgSO4. The solvent was then removed under reduced pressure and the residue was purified by column chromatography on silica gel eluting with ethyl acetate in hexane. The solvent in the eluent was evaporated to give 5.4 g of a yellow solid which was used without further purification.

来源