تفاعل #82222

معادلة التفاعل

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

4-chloropyridine hydrochloride

isopropanol

→

desired product

المردود 33.0%

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

المردود 33.0%

ظروف التفاعل

المعالجة

1. 1
   أخرىThe flask was flushed with nitrogen
2. 2
   أخرىfitted with a condensor and nitrogen inlet
3. 3
   درجة الحرارةThe reaction mixture was heated
4. 4
   درجة الحرارةat reflux for 9 hours
5. 5
   workup.ADDITIONthe reaction mixture was poured into dilute aqueous sodium bicarbonate
6. 6
   استخلاصThe product was extracted thrice with ethyl acetate
7. 7
   غسيلThe combined organic layers were washed with brine
8. 8
   تجفيفdried (K2CO3)
9. 9
   ترشيحFiltration and concentration
10. 10
    أخرىgave the crude product
11. 11
    أخرىPurification via flash column chromatography (silica gel, 2% Et3N/0-2% MeOH/ether)

الإجراء التجريبي

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.

المصدر