Methanol → HCID 15719002, compound

HRID 1073086Notes

Reaction equation

HRID 1073086 reaction equation
C([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([C:13]#N)[CH:8]=1)(=O)C.[OH-:15].[K+].[CH3:17][OH:18]>>[OH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([C:13]([O:18][CH3:17])=[O:15])[CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 22157968HCID 22157968, compound

Product 1

HCID 15719002HCID 15719002, compound

Procedure

A 1 l. round bottom flask was charged with 18.24 g (0.096 mol) of 4-[2-(acetyloxy)ethyl]-2-pyridinecarbonitrile and 380 ml of methanol. To the reaction mixture was added 96 ml of 5N aqueous potassium hydroxide and the reaction mixture was refluxed overnight with stirring. The reaction mixture was cooled and concentrated under vacuum. To the residue was added methanol saturated with hydrochloric acid (400 ml), and the resulting mixture was heated to reflux for 30 minutes, cooled and concentrated under vacuum. To the residue was added 400 ml of methanol saturated with hydrochloric acid. The mixture was refluxed overnight, cooled to room temperature and concentrated under vacuum. The mixture was partitioned between methylene chloride and 20% by weight potassium bicarbonate in water. The organic layer was separated, and the aqueous layer was extracted three times with methylene chloride and one time with diethyl ether. The organic extracts were combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to provide 11.51 g of the desired compound. The aqueous layer was concentrated to approximately half its original volume, extracted three times with methylene chloride and one time with diethyl ether. The organic extracts were combined, dried over anhydrous sodium sulfate and concentrated under vacuum as described above to provide an additional 1.15 g of the desired compound. The crude products were combined and purified by high pressure liquid chromatography to provide 9.02 g of methyl 4-(2-hydroxyethyl)-2-pyridinecarboxylate as a clear oil.

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated under vacuum
  4. additionTo the residue was added methanol saturated with hydrochloric acid (400 ml)
  5. temperaturethe resulting mixture was heated
  6. temperatureto reflux for 30 minutes
  7. temperaturecooled
  8. concentrationconcentrated under vacuum
  9. additionTo the residue was added 400 ml of methanol saturated with hydrochloric acid
  10. temperatureThe mixture was refluxed overnight
  11. concentrationconcentrated under vacuum
  12. customThe mixture was partitioned between methylene chloride and 20% by weight potassium bicarbonate in water
  13. customThe organic layer was separated
  14. extractionthe aqueous layer was extracted three times with methylene chloride and one time with diethyl ether
  15. dry with materialdried over anhydrous sodium sulfate
  16. filtrationfiltered
  17. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8e660b9c286e429899256e88cef39d38
Source dataset
uspto-grants-1990_11
Patent number
US04968678

Reaction notes

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