Reaktion #593044

Reaktionsgleichung

n-butyllithium

potassium hydroxide

acridine

TMEDA

→

yellow powder

Ausbeute 83.0%

9-butylacridine

Ausbeute 83.0%

Lösungsmittel

acetonitrile

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigequenched with water
2. 2
   workup.STIRRINGAfter stirring for an additional 0.5 hour
3. 3
   workup.ADDITIONthe reaction mixture was poured into ice-water
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   WaschenThe organic layer was washed with water several times
6. 6
   Trocknendried over MgSO4
7. 7
   SonstigeRemoval of solvent
8. 8
   Sonstigeafforded a residue
9. 9
   ExtraktionThe mixture was extracted with ethyl acetate
10. 10
    Trocknendried over MgSO4
11. 11
    SonstigeAfter evaporation of the solvent
12. 12
    Sonstigethe crude product was purified by chromatography on silica gel (hexanes:ethyl acetate=10:1 as eluent)

Vorschrift

To an ice-cooled solution of acridine (24.8 g, 0.139 mol) and TMEDA (N,N,N′,N′-tetramethylethylenediamine) (5.0 ml, 0.034 mol) in THF (160 mL), was slowly added 2.5 M n-butyllithium in hexanes (162 mL, 0.405 mol). The resulting solution was stirred at 0° C. for 2 hours and quenched with water. After stirring for an additional 0.5 hour, the reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with water several times and dried over MgSO4. Removal of solvent afforded a residue. This residue was taken up in acetonitrile (700 mL) and treated with potassium ferricyanide (198.0 g, 0.601 mol) aqueous solution (1110 mL) containing potassium hydroxide (99.0 g, 1.764 mol) for about 42 hours at room temperature. The mixture was extracted with ethyl acetate and dried over MgSO4. After evaporation of the solvent, the crude product was purified by chromatography on silica gel (hexanes:ethyl acetate=10:1 as eluent) to afford 27.0 g (83%) of yellow powder.

Quelle