N-methyl-2-pyrrolidone → 3-(5-Bromopyridine-3-carbonyl)-1-methylpyrrolidin-2-one
Reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([CH:13]=1)[C:9]([O:11]C)=O.[CH3:14][N:15]1[CH2:19][CH2:18][CH2:17][C:16]1=[O:20].[Cl-].[NH4+]>C1(C)C=CC=CC=1>[Br:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([CH:13]=1)[C:9]([CH:17]1[CH2:18][CH2:19][N:15]([CH3:14])[C:16]1=[O:20])=[O:11]Participants
Procedure
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).
Workup
- washwas washed with toluene (3×10 ml) under nitrogen atmosphere
- temperatureThe resulting slurry in 50 ml of toluene was refluxed for 30 minutes under nitrogen and to it
- temperatureThen the reaction mixture was refluxed for 10 h
- dry with materialThe separated organic layer was dried over with sodium sulfate
- filtrationfiltered
- customevaporated under reduced pressure
- customto obtain crude residue which
- customwas purified by silica-gel column chromatography
Sources & evidence
- ORD record
- ord-bbcb7b39e8b947d69b2ed6bcb2668d66
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08754228B2
Reaction notes
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