Water → HCID 86754878, compound

HRID 1604538Notes

Reaction equation

HRID 1604538 reaction equation
[H-].[Na+].[C:3]([NH:6][C:7]1[N:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=1)(=[O:5])[CH3:4].[CH3:19]I.O>CN(C)C=O>[CH3:19][N:6]([C:7]1[N:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=1)[C:3](=[O:5])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86754877HCID 86754877, compound

Product 1

HCID 86754878HCID 86754878, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (60% in oil, 20.6 mg) in N,N-dimethylformamide (1 ml) was added dropwise a solution of methyl (E)-3-(6-acetylaminopyridin-3-yl)acrylate (180 mg) in N,N-dimethylformamide (2 ml) at 0° C. under nitrogen and the mixture was stirred for 1 hour. Methyl iodide (116 mg) was added to the mixture under the same condition and the mixture was stirred for 2 hours. 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 evaporated in vacuo. The residue was collected by vacuum filtration and washed with diisopropyl ether to give methyl (E)-3-[6-(N-methyl-N-acetylamino)pyridin-3-yl]acrylate (115 mg) as a powder.

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. filtrationThe residue was collected by vacuum filtration
  7. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-bfe280e3b80340d6be122f66d4fd0791
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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