Methanol → HCID 10749820, compound

HRID 1604568Notes

Reaction equation

HRID 1604568 reaction equation
[CH3:1]O.S(Cl)(Cl)=O.[NH2:7][C:8]1[N:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([OH:18])=[O:17])=[CH:10][CH:9]=1>C(=O)=O.CC(C)=O>[NH2:7][C:8]1[N:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([O:18][CH3:1])=[O:17])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 10487224(2E)-3-(6-aminopyridin-3-yl)prop-2-enoic acid

Product 1

HCID 10749820HCID 10749820, compound

Reagents, catalysts & solvents 1

HCID 18522661Acetone cardiceSolvent

Procedure

To methanol (5 ml) in dry ice-acetone bath was added thionyl chloride (0.41 ml) dropwise over 5 minutes. After (E)-3-(6-Aminopyridin-3-yl)acrylic acid (700 mg) was added to the mixture, the reaction mixture was heated at reflux for 1 hour, and the solvent was removed under reduced pressure. The reaction mixture was adjusted to pH 8 with saturated sodium bicarbonate aqueous solution and extracted with dichloromethane. The organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The precipitate was collected by vacuum filtration and washed with isopropyl ether to give methyl (E)-3-(6-aminopyridin-3-yl)acrylate (725 mg) as a solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 1 hour
  3. customthe solvent was removed under reduced pressure
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. filtrationThe precipitate was collected by vacuum filtration
  9. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-401d477f21db4bd0966514f77e9f3050
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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