Réaction #82222

Équation de réaction

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

4-chloropyridine hydrochloride

isopropanol

→

desired product

Rendement 33.0%

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

Rendement 33.0%

Conditions de réaction

Traitement

1. 1
   AutreThe flask was flushed with nitrogen
2. 2
   Autrefitted with a condensor and nitrogen inlet
3. 3
   TempératureThe reaction mixture was heated
4. 4
   Températureat reflux for 9 hours
5. 5
   workup.ADDITIONthe reaction mixture was poured into dilute aqueous sodium bicarbonate
6. 6
   ExtractionThe product was extracted thrice with ethyl acetate
7. 7
   LavageThe combined organic layers were washed with brine
8. 8
   Séchagedried (K2CO3)
9. 9
   FiltrationFiltration and concentration
10. 10
    Autregave the crude product
11. 11
    AutrePurification via flash column chromatography (silica gel, 2% Et3N/0-2% MeOH/ether)

Mode opératoire

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.

Source