반응 #82222

반응 방정식

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

4-chloropyridine hydrochloride

isopropanol

→

desired product

수율 33.0%

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

수율 33.0%

반응 조건

후처리

1. 1
   기타The flask was flushed with nitrogen
2. 2
   기타fitted with a condensor and nitrogen inlet
3. 3
   온도The reaction mixture was heated
4. 4
   온도at reflux for 9 hours
5. 5
   workup.ADDITIONthe reaction mixture was poured into dilute aqueous sodium bicarbonate
6. 6
   추출The product was extracted thrice with ethyl acetate
7. 7
   세척The combined organic layers were washed with brine
8. 8
   건조dried (K2CO3)
9. 9
   여과Filtration and concentration
10. 10
    기타gave the crude product
11. 11
    기타Purification via flash column chromatography (silica gel, 2% Et3N/0-2% MeOH/ether)

실험 절차

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.

출처