Ammonia → (Z)-3-Amino-2-methyl-2-butenoic Acid Ethyl Ester

HRID 2231947Notes

Reaction equation

HRID 2231947 reaction equation
C[CH2:2][C:3](=O)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH3:11].[CH3:12]CO>>[CH2:8]([O:7][C:5](=[O:6])/[C:4](/[CH3:12])=[C:3](\[NH2:11])/[CH3:2])[CH3:9]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 702EthanolHCID 78656Ethyl 3-oxovalerate

Product 1

HCID 53642952(Z)-3-Amino-2-methyl-2-butenoic Acid Ethyl Ester

Conditions

Temperature
80 °C

Procedure

10 kg ethyl methylacetoacetate and 4 l abs. etanol was mixed in an autoclave and 3.4 kg of liquid ammonia was added. The mixture is stirred and the temperature gradually increased to 80° C. during 4 hrs. This temperature is maintained over night. The temperature is decreased to 40° C. and the excess ammonia is evaporated. Toluene (10 l) is added and the water is separated. The organic layer is dried by evaporation of toluene and alcohol. The yield is quantitative. The product is low melting solid.

Workup

  1. additionwas added
  2. temperatureThis temperature is maintained over night
  3. customis decreased to 40° C.
  4. customthe excess ammonia is evaporated
  5. additionToluene (10 l) is added
  6. customthe water is separated
  7. dry with materialThe organic layer is dried by evaporation of toluene and alcohol

Sources & evidence

ORD record
ord-e03057c3a1a54a968a22e32680b537a4
Source dataset
uspto-grants-1988_11
Patent number
US04785113

Reaction notes

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