Malonic Acid → 3-amino-3-[4-(trifluoromethoxy)phenyl]propanoic Acid

HRID 1368902Notes

Reaction equation

HRID 1368902 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1.[C:14]([OH:20])(=[O:19])[CH2:15]C(O)=O.C([O-])(=O)C.[NH4+:25]>C(O)C>[NH2:25][CH:8]([C:7]1[CH:10]=[CH:11][C:4]([O:3][C:2]([F:13])([F:12])[F:1])=[CH:5][CH:6]=1)[CH2:15][C:14]([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 69573p-(Trifluoromethoxy)benzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 27684603-amino-3-[4-(trifluoromethoxy)phenyl]propanoic Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10.5 g of 4-(trifluoromethoxy)benzaldehyde, 5.72 g of malonic acid, 8.5 g of ammonium acetate and 40 ml of ethanol are boiled under reflux for 8 hours and stirred at room temperature overnight. The cooled reaction mixture is then filtered with suction, washed with ethanol and ether and dried in air. 3-amino-3-(4-trifluoromethoxyphenyl)propionic acid is obtained, melting point 258-260°.

Workup

  1. temperatureunder reflux for 8 hours
  2. customThe cooled reaction mixture
  3. filtrationis then filtered with suction
  4. washwashed with ethanol and ether
  5. customdried in air

Sources & evidence

ORD record
ord-f0605d84d90b43599d714c85a74a8d39
Source dataset
uspto-grants-2003_06
Patent number
US06576637B1

Reaction notes

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