Malonic Acid → 3-Amino-3-(3,4-difluorophenyl)propanoic acid

HRID 2268028Notes

Reaction equation

HRID 2268028 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=O.[C:11]([OH:17])(=[O:16])[CH2:12]C(O)=O.C([O-])(=O)C.[NH4+:22]>C(O)C>[NH2:22][CH:5]([C:4]1[CH:7]=[CH:8][C:9]([F:10])=[C:2]([F:1])[CH:3]=1)[CH2:12][C:11]([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 517165Ammonium AcetateHCID 5880883,4-Difluorobenzaldehyde

Product 1

HCID 183487173-Amino-3-(3,4-difluorophenyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,4-Difluorobenzaldehyde (7.76 mL, 70.3 mmol), malonic acid (7.28 g, 70.3 mmol), and ammonium acetate (10.79 g, 140 mmol) were combined in absolute ethanol (30 mL) and refluxed under nitrogen for 6 hours. The mixture was cooled and stirred at ambient temperature overnight. A white solid precipitated which was collected by filtration to yield the title compound.

Workup

  1. temperaturerefluxed under nitrogen for 6 hours
  2. temperatureThe mixture was cooled
  3. customA white solid precipitated which
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-b8ce11ee15cc4ae69a7e81715562d2d3
Source dataset
uspto-grants-2001_12
Patent number
US06326372B1

Reaction notes

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