Ethanol → Ethyl 3-amino-3-(pyridin-3-yl)propanoate

HRID 261093Notes

Reaction equation

HRID 261093 reaction equation
[NH2:1][CH:2]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[CH2:3][C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH2:18](O)[CH3:19]>>[NH2:1][CH:2]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[CH2:3][C:4]([O:6][CH2:18][CH3:19])=[O:5]

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 1118Sulfuric AcidHCID 36065473-Amino-3-(pyridin-3-yl)propanoic acid

Product 1

HCID 15223455Ethyl 3-amino-3-(pyridin-3-yl)propanoateYield 65%

Procedure

To a stirred suspension of 114 g (0.69 mole) of β-amino-β-(3-pyridyl)propionic acid in 2,850 ml of ethanol was added a 5° C. solution of 417 g of sulfuric acid in 240 ml of ethanol. After stirring for 1 hour, the resultant clear solution was left standing at room temperature for 48 hours and then concentrated to incipient crystallization in vacuum at a temperature below 50° C. The solution was added to a suspension of 715 g of sodium bicarbonate in 1430 ml of water over 1 hour. The temperature of the solution was maintained between 0° to 5° C. After stirring an additional 30 minutes, 300 ml of carbon tetrachloride was added and the admixture stirred for 10 minutes. The by-product salt was removed by filtration and the aqueous layer was extracted thoroughly with carbon tetrachloride. The combined organic extracts were dried and concentrated under vacuum to yield 87.11 g (65% yield) of crude ethyl β-amino-β-(3-pyridyl)propionate as a slightly viscous green liquid.

Workup

  1. waitthe resultant clear solution was left
  2. waitstanding at room temperature for 48 hours
  3. concentrationconcentrated
  4. customcrystallization in vacuum at a temperature below 50° C
  5. additionThe solution was added to a suspension of 715 g of sodium bicarbonate in 1430 ml of water over 1 hour
  6. temperatureThe temperature of the solution was maintained between 0° to 5° C
  7. stirringAfter stirring an additional 30 minutes
  8. addition300 ml of carbon tetrachloride was added
  9. stirringthe admixture stirred for 10 minutes
  10. customThe by-product salt was removed by filtration
  11. extractionthe aqueous layer was extracted thoroughly with carbon tetrachloride
  12. customThe combined organic extracts were dried
  13. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-20424e0039d5463fa52c2059ea593b56
Source dataset
uspto-grants-1979_08
Patent number
US04163855

Reaction notes

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