反応 #1379891

反応方程式

5-aminoquinoline

acetaldehyde

4-thiocresol

→

yellow solid

収率 62.7%

ethylquinolin-5-yl-amine

収率 62.7%

溶媒

ethanol

反応条件

後処理

1. 1
   温度at reflux for 4 h
2. 2
   その他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
    抽出the product was extracted with dichloromethane (4×100 ml)
12. 12
    洗浄washed with water (250 ml)
13. 13
    乾燥before being dried over MgSO4
14. 14
    その他The solvent was then removed under reduced pressure
15. 15
    その他the residue was purified by column chromatography on silica gel eluting with ethyl acetate in hexane
16. 16
    その他The solvent in the eluent was evaporated

実験手順

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.

出典