HCID 53666228, compound → HCID 53880921, compound

HRID 728314Notes

Reaction equation

HRID 728314 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][C:6](C#N)([C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1)[CH2:7][CH2:8][C:9]([OH:11])=[O:10]>Cl>[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][CH:6]([C:12]1[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=1)[CH2:7][CH2:8][C:9]([OH:11])=[O:10]

Participants

3

Reactant 1

HCID 53666228HCID 53666228, compound

Product 1

HCID 53880921HCID 53880921, compoundYield 219.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Into 250 ml of concentrated hydrochloric acid, 13 g of 4-cyano-4-(4-pyridyl)pimelic acid methyl ester was dissolved, and the solution was refluxed for 14 hours. Hydrochloric acid was distilled off under reduced pressure and the residue was dissolved in 200 ml of methanol. To this solution, there was added 1 ml of concentrated sulfuric acid and the mixture was refluxed for 4 hours. After 3 g of sodium bicarbonate was added, methanol was distilled off and 150 ml of water and 150 ml of ethyl acetate were added. Further, 25 g of sodium bicarbonate was gradually added. The organic layer was removed, washed with 50 ml of saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. After the solvent was distilled off, there was obtained 26 g of 4-(4-pyridyl)pimelic acid methyl ester as an oily material.

Workup

  1. temperaturethe solution was refluxed for 14 hours
  2. distillationHydrochloric acid was distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in 200 ml of methanol
  4. additionTo this solution, there was added 1 ml of concentrated sulfuric acid
  5. temperaturethe mixture was refluxed for 4 hours
  6. additionAfter 3 g of sodium bicarbonate was added
  7. distillationmethanol was distilled off
  8. addition150 ml of water and 150 ml of ethyl acetate were added
  9. additionFurther, 25 g of sodium bicarbonate was gradually added
  10. customThe organic layer was removed
  11. washwashed with 50 ml of saturated aqueous solution of sodium chloride
  12. dry with materialdried over anhydrous sodium sulfate
  13. distillationAfter the solvent was distilled off

Sources & evidence

ORD record
ord-f1ac59fbe89c4fd989eb921a3b5d80c6
Source dataset
uspto-grants-1991_09
Patent number
US05047545

Reaction notes

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