Ammonia → 3-Amino-3-cyclopropyl-acrylic acid ethyl ester

HRID 1084894Notes

Reaction equation

HRID 1084894 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:12]1([C:15]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=O)[CH2:14][CH2:13]1.[NH3:23].O>C1(C)C=CC=CC=1>[NH2:23][C:15]([CH:12]1[CH2:14][CH2:13]1)=[CH:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 262979Ethyl 3-cyclopropyl-3-oxopropanoate

Product 1

HCID 534018893-Amino-3-cyclopropyl-acrylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.1 g of p-toluenesulphonic acid are added to 49.9 g (0.32 mol) of ethyl cyclopropylcarbonylacetate in 200 ml of dry toluene and the mixture is saturated with ammonia gas at room temperature with stirring. After allowing to stand overnight, the mixture is heated under reflux for 8 h in a water separator, ammonia gas being continuously introduced. The mixture is allowed to cool overnight and is filtered, and the toluene solution is concentrated in vacuo and distilled from unreacted starting material in a high vacuum up to 65° C. The substance is subsequently found in the residue.

Workup

  1. temperaturethe mixture is heated
  2. additioncontinuously introduced
  3. temperatureto cool overnight
  4. filtrationis filtered
  5. concentrationthe toluene solution is concentrated in vacuo
  6. distillationdistilled
  7. customup to 65° C

Sources & evidence

ORD record
ord-82cfed62981645f8820810b32dc93b68
Source dataset
uspto-grants-1991_04
Patent number
US05006530

Reaction notes

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