Trimethylsilyldiazomethane → HCID 86754877, compound

HRID 1604537Notes

Reaction equation

HRID 1604537 reaction equation
[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([OH:15])=[O:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH3:16][Si](C=[N+]=[N-])(C)C>ClCCl.CO>[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([O:15][CH3:16])=[O:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 10703461(E)-3-(6-Acetamidopyridin-3-YL)acrylic acid

Product 1

HCID 86754877HCID 86754877, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of (E)-3-(6-acetylaminopyridin-3-yl)acrylic acid (200 mg) in a mixture of dichloromethane (3 ml) and methanol (3 ml) was added a solution of 10% trimethylsilyldiazomethane (3 ml) at ambient temperature and the mixture was stirred for 3 hours. The reaction mixture was evaporated in vacuo, poured into water and extracted with dichloromethane. 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-acetylaminopyridin-3-yl)acrylate (197 mg) as a powder.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. additionpoured into water
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. filtrationThe residue was collected by vacuum filtration
  8. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-f86d8e8f1fa040e4b8d4e413245c68b6
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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