Reaktion #82222

Reaktionsgleichung

1-amino-1,3-dihydro-3,3-dimethyl-2H-indol-2-one

4-chloropyridine hydrochloride

isopropanol

→

desired product

Ausbeute 33.0%

1,3-Dihydro-3,3-dimethyl-1-(propyl-4-pyridinylamino)-2H-indol-2-one

Ausbeute 33.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe flask was flushed with nitrogen
2. 2
   Sonstigefitted with a condensor and nitrogen inlet
3. 3
   TemperaturThe reaction mixture was heated
4. 4
   Temperaturat reflux for 9 hours
5. 5
   workup.ADDITIONthe reaction mixture was poured into dilute aqueous sodium bicarbonate
6. 6
   ExtraktionThe product was extracted thrice with ethyl acetate
7. 7
   WaschenThe combined organic layers were washed with brine
8. 8
   Trocknendried (K2CO3)
9. 9
   FiltrationFiltration and concentration
10. 10
    Sonstigegave the crude product
11. 11
    SonstigePurification via flash column chromatography (silica gel, 2% Et3N/0-2% MeOH/ether)

Vorschrift

To a stirred solution of 1-amino-1,3-dihydro-3,3-dimethyl-2H-indol-2-one (7.35 g) and isopropanol (167 ml) was added 4-chloropyridine hydrochloride (8.15 g). The flask was flushed with nitrogen and fitted with a condensor and nitrogen inlet. The reaction mixture was heated at reflux for 9 hours. Upon cooling to room temperature, the reaction mixture was poured into dilute aqueous sodium bicarbonate. The product was extracted thrice with ethyl acetate and once with dichloromethane. The combined organic layers were washed with brine and dried (K2CO3). Filtration and concentration gave the crude product. Purification via flash column chromatography (silica gel, 2% Et3N/0-2% MeOH/ether) afforded 3.5 g (33%) of the desired product.

Quelle