Ethanol → Ethyl 3-amino-3-(2-fluorophenyl)-2-propenoate

HRID 1196760Notes

Reaction equation

HRID 1196760 reaction equation
C(OC(=O)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][CH3:13])[C:7]=1[F:14])(=O)C.[C:16]([O-:19])(=[O:18])C.[NH4+:20].[CH2:21](O)[CH3:22]>C(O)(=O)C>[NH2:20][C:12]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:6][C:7]=1[F:14])=[CH:13][C:16]([O:19][CH2:21][CH3:22])=[O:18]

Participants

5

Reactant 3

HCID 702EthanolHCID 517165Ammonium AcetateHCID 54187082HCID 54187082, compound

Product 1

HCID 67835821Ethyl 3-amino-3-(2-fluorophenyl)-2-propenoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
10 °C

Procedure

52.5 g of ethyl(2-fluorobenzoyl) acetate and 96.3 g of ammonium acetate were added to 250 ml of ethanol, followed by dropwise addition of 75.0 g of acetic acid to the solution with stirring at 10° C. The resulting solution was heated to room temperature and then stirred under reflux for 4 hours. After the reaction was completed, the solvent was distilled away under reduced pressure and the residue was dissolved in diethyl ether. This ether solution was washed with dilute hydrochloric acid, water and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The solvent was distilled away to obtain 50.5 g of ethyl 3-amino-3-(2-fluorophenyl)-2-propenoate.

Workup

  1. temperatureThe resulting solution was heated to room temperature
  2. stirringstirred
  3. temperatureunder reflux for 4 hours
  4. distillationthe solvent was distilled away under reduced pressure
  5. dissolutionthe residue was dissolved in diethyl ether
  6. washThis ether solution was washed with dilute hydrochloric acid, water
  7. dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled away

Sources & evidence

ORD record
ord-7ef92dc7ee684db9aa4e01cc9c6b7e0d
Source dataset
uspto-grants-1992_05
Patent number
US05116404

Reaction notes

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