Reaktion #1379891

Reaktionsgleichung

5-aminoquinoline

acetaldehyde

4-thiocresol

→

yellow solid

Ausbeute 62.7%

ethylquinolin-5-yl-amine

Ausbeute 62.7%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle