Malonic Acid → 3-amino-3-(3,5-dimethoxyphenyl)propanoic Acid

HRID 1371532Notes

Reaction equation

HRID 1371532 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[CH:6]=O.[C:13]([OH:19])(=[O:18])[CH2:14]C(O)=O.C([O-])(=O)C.[NH4+:24]>CCO>[NH2:24][CH:6]([C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=1)[CH2:14][C:13]([OH:19])=[O:18]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 817473,5-DimethoxybenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 51077633-amino-3-(3,5-dimethoxyphenyl)propanoic AcidYield 43.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5 g of 3,5-dimethoxybenzaldehyde, 3.13 g of malonic acid and 4.64 g of ammonium acetate in 50 ml of EtOH is refluxed for 5 hours. The reaction mixture is concentrated under vacuum, the residue is taken up in water, insoluble material is filtered off, the filtrate is washed with DCM and the aqueous phase is concentrated under vacuum. The residue is taken up in water and concentrated under vacuum again. The residue is taken up in EtOH and the solvent is evaporated off under vacuum. 2.96 g of the expected product are obtained.

Workup

  1. temperatureis refluxed for 5 hours
  2. concentrationThe reaction mixture is concentrated under vacuum
  3. filtrationinsoluble material is filtered off
  4. washthe filtrate is washed with DCM
  5. concentrationthe aqueous phase is concentrated under vacuum
  6. concentrationconcentrated under vacuum again
  7. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-1c0d8a62e6b74221897c5e02de84f316
Source dataset
uspto-grants-2007_01
Patent number
US07157454B2

Reaction notes

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