Water → HCID 10634150, compound

HRID 1604570Notes

Reaction equation

HRID 1604570 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[N:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([O:18][CH3:19])=[O:17])=[CH:10][CH:9]=1)=[O:6].[H-].[Na+].O>CN(C)C=O>[O:6]=[C:5]1[CH2:4][CH2:3][CH2:2][N:7]1[C:8]1[N:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([O:18][CH3:19])=[O:17])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 10496423HCID 10496423, compound

Product 1

HCID 10634150HCID 10634150, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl (E)-3-[6-(4-bromobutyramido)-pyridin-3-yl]acrylate (90 mg) in dimethylformamide was added sodium hydride (6.93 mg) at 0° C. under nitrogen atmosphere, and the mixture was stirred for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo to give methyl (E)-3-[6-(2-oxopyrrolidin-1-yl)pyridin-3-yl]acrylate (65 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c561cc6d3ff941cba12380f955342127
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

Loading…