Réaction #1379891

Équation de réaction

5-aminoquinoline

acetaldehyde

4-thiocresol

→

yellow solid

Rendement 62.7%

ethylquinolin-5-yl-amine

Rendement 62.7%

Solvants

ethanol

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source