Ammonia → ethyl 3-iminobutanoate

HRID 1842352Notes

Reaction equation

HRID 1842352 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[NH3:10]>>[NH:10]=[C:3]([CH3:5])[CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 8868Ethyl Acetoacetate

Product 1

HCID 319843ethyl 3-iminobutanoateYield 85%

Procedure

A solution of ethyl acetoacetate (50 g, 385 mmol, 1.0 eq) in 25% aqueous ammonia (300 mL) was stirred at room temperature for 1 h then extracted with EtOAc (2×300 mL). The combined organic layers were dried over Na2SO4 and the solvent was removed under reduced pressure to give ethyl 3-iminobutanoate (42 g, 85%) as a yellow oil, which was used directly in the next step.

Workup

  1. extractionthen extracted with EtOAc (2×300 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-316853aa0d564befa2ea8fc6da03ba74
Source dataset
uspto-grants-2015_02
Patent number
US08946224B2

Reaction notes

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