반응 #1379891

반응 방정식

5-aminoquinoline

acetaldehyde

4-thiocresol

→

yellow solid

수율 62.7%

ethylquinolin-5-yl-amine

수율 62.7%

용매

ethanol

반응 조건

후처리

1. 1
   온도at reflux for 4 h
2. 2
   기타The 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
   온도maintaining the temperature below 5° C
6. 6
   workup.STIRRINGThis reaction mixture was stirred
7. 7
   온도at 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
    온도at reflux
11. 11
    추출the product was extracted with dichloromethane (4×100 ml)
12. 12
    세척washed with water (250 ml)
13. 13
    건조before being dried over MgSO4
14. 14
    기타The solvent was then removed under reduced pressure
15. 15
    기타the residue was purified by column chromatography on silica gel eluting with ethyl acetate in hexane
16. 16
    기타The solvent in the eluent was evaporated

실험 절차

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.

출처