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

HRID 1073111Notes

Reaction equation

HRID 1073111 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 boiled under reflux for 8 hours 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 removed by distillation in a high vacuum up to 65° C. from unreacted starting material. The substance is subsequently found in the residue. Yield: 11.9 g (24% of theory).

Workup

  1. additioncontinuously introduced
  2. temperatureto cool overnight
  3. filtrationis filtered
  4. concentrationthe toluene solution is concentrated in vacuo
  5. customremoved by distillation in a high vacuum up to 65° C.

Sources & evidence

ORD record
ord-bc752135b5394e99b93c7e180cb74a74
Source dataset
uspto-grants-1990_11
Patent number
US04968689

Reaction notes

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