Malonic Acid → 3-Amino-3-(4-fluorophenyl)propanoic acid

HRID 846199Notes

Reaction equation

HRID 846199 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([OH:16])(=[O:15])[CH2:11]C(O)=O.C([O-])(=O)C.[NH4+:21]>C(O)C>[NH2:21][CH:6]([C:5]1[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=1)[CH2:11][C:10]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 680234-FluorobenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 5798853-Amino-3-(4-fluorophenyl)propanoic acidYield 23.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 24.8 g (0.2 mol) of 4-fluorobenzaldehyde, 20.8 g (0.2 mol) of malonic acid, 30.8 g (0.4 mol) of ammonium acetate and 550 ml of ethanol was refluxed for approximately seven hours. The mixture was cooled and the precipitated solid was collected by vacuum filtration. The solid was recrystallized from 500 ml of water to provide 8.66 g of 3-amino-3-(4-fluorophenyl)propionic acid. mp=225° C. dec.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe precipitated solid was collected by vacuum filtration
  3. customThe solid was recrystallized from 500 ml of water

Sources & evidence

ORD record
ord-a69e73985bce4a68ba141535975245a6
Source dataset
uspto-grants-1992_08
Patent number
US05135947

Reaction notes

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