反応 #163567

反応方程式

ammonium chloride

methyl 5-bromonicotinate

1-methyl-2-pyrrolidone

NaH

→

solid

収率 24.4%

3-(5-bromonicotinoyl)-1-methylpyrrolidin-2-one

収率 24.4%

溶媒

toluene

反応条件

後処理

1. 1
   洗浄was washed with toluene (3×10 ml) under nitrogen atmosphere
2. 2
   温度The resulting slurry in 50 ml of toluene was refluxed for 30 minutes under nitrogen and to it
3. 3
   温度Then the reaction mixture was refluxed for 10 h
4. 4
   乾燥The separated organic layer was dried over with sodium sulfate
5. 5
   ろ過filtered
6. 6
   その他evaporated under reduced pressure
7. 7
   その他to obtain crude residue which
8. 8
   その他was purified by silica-gel column chromatography

実験手順

A suspension of NaH (60% in oil, 1.84 g, 46 mmol) was washed with toluene (3×10 ml) under nitrogen atmosphere. The resulting slurry in 50 ml of toluene was refluxed for 30 minutes under nitrogen and to it was added slowly a toluene (25 ml) solution of methyl 5-bromonicotinate (5 g, 23.26 mmol) and 1-methyl-2-pyrrolidone (4.58 g, 46.5 mmol) for 45 minutes. Then the reaction mixture was refluxed for 10 h. After completion of the reaction cooled to room temperature and added 10 ml of saturated ammonium chloride. The separated organic layer was dried over with sodium sulfate, filtered and evaporated under reduced pressure to obtain crude residue which was purified by silica-gel column chromatography using EtOAc/hexane (60:40) as an eluent to afford an off white solid (1.6 g, 24.4% yield).

出典