Sodium → ethyl beta-[N-(2-dimethylaminoethyl)-2-oxo-4-pyridyl]propionate

HRID 1719550Notes

Reaction equation

HRID 1719550 reaction equation
[Na].[OH:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:5][N:4]=1.Cl.[CH3:17][N:18]([CH2:20][CH2:21]Cl)[CH3:19]>C(O)C>[CH3:17][N:18]([CH3:19])[CH2:20][CH2:21][N:4]1[CH:5]=[CH:6][C:7]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][C:3]1=[O:2]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 178471091HCID 178471091, compound

Product 1

HCID 20267139ethyl beta-[N-(2-dimethylaminoethyl)-2-oxo-4-pyridyl]propionateYield 64.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To a cooled solution of sodium (7.50 g) in ethanol (150 ml) was added a solution of ethyl β-(2-hydroxy-4-pyridyl)propionate (29.07 g) in ethanol (175 ml). After the solution was stirred for 40 minutes a solution of dimethylaminoethyl chloride hydrochloride (21.78 g) in ethanol (175 ml) was added and the reaction mixture was stirred under reflux for 6 hours and then was allowed to cool overnight. The reaction mixture was filtered and evaporated under reduced pressure to remove most of the solvent. Water (150 ml) was added and the solution was extracted with ethyl acetate (3×200 ml). The combined ethyl acetate extracts were dried over MgSO4 and evaporated under reduced pressure to yield an oil which was subjected to medium pressure column chromatography (using Kieselgel 60 silica gel 70-230 mesh-pre column and 230-400 mesh-main column) with gradient elution (dichloromethane→10% methanolic dichloromethane). The fractions containing the desired product were combined and evaporated under reduced pressure to yield ethyl β-[N-(2 -dimethylaminoethyl)-2-oxo-4-pyridyl]propionate (25.43 g) as an oil.

Workup

  1. additionwas added
  2. temperatureunder reflux for 6 hours
  3. temperatureto cool overnight
  4. filtrationThe reaction mixture was filtered
  5. customevaporated under reduced pressure
  6. customto remove most of the solvent
  7. additionWater (150 ml) was added
  8. extractionthe solution was extracted with ethyl acetate (3×200 ml)
  9. dry with materialThe combined ethyl acetate extracts were dried over MgSO4
  10. customevaporated under reduced pressure
  11. customto yield an oil which
  12. washwas subjected to medium pressure column chromatography (using Kieselgel 60 silica gel 70-230 mesh-pre column and 230-400 mesh-main column) with gradient elution (dichloromethane→10% methanolic dichloromethane)
  13. additionThe fractions containing the desired product
  14. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b873ffcc5b4e46c2b3485c8554eed8aa
Source dataset
uspto-grants-1985_09
Patent number
US04540699

Reaction notes

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