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

HRID 1486253Notes

Reaction equation

HRID 1486253 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 acidYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

697 g of 3,4-difluorobenzaldehyde (4.76 mol, 1 equivalent) were stirred together with 495 g of malonic acid (4.76 mol, 1 equivalent) and 733 g of ammonium acetate (9.52 mol, 2 equivalents) in 2788 ml of ethanol at reflux under argon for 20 h. Then the mixture was cooled to RT and stirred at RT overnight. The precipitated crystals were filtered off with suction, washed with ethanol and diethyl ether, and dried under reduced pressure. 590 g (62% of theory) of rac-3-amino-3-(3,4-difluorophenyl)propanoic acid were obtained.

Workup

  1. temperatureat reflux under argon for 20 h
  2. filtrationThe precipitated crystals were filtered off with suction
  3. washwashed with ethanol and diethyl ether
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-49ddada4bdb9485291c667c93e036a3e
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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