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

HRID 1941235Notes

Reaction equation

HRID 1941235 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=O.[C:13]([O-:16])(=[O:15])[CH3:14].[NH4+:17].C(O)(=O)CC(O)=O>C(O)C>[NH2:17][CH:6]([C:5]1[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:14][C:13]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8419VeratraldehydeHCID 517165Ammonium Acetate

Product 1

HCID 5971823-Amino-3-(3,4-dimethoxyphenyl)propanoic acidYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred suspension of 3,4-dimethoxybenzaldehyde (131 grams, 788 mmol) and ammonium acetate (121.5 grams, 1576 mmol) in ethanol (95%, 400 mL) was heated to 45°-50° C. resulting in an orange solution. To this solution was added malonic acid (82.0 grams, 788 mmol) and the solution was refluxed overnight. A white solid precipitated on heating, the slurry was allowed to cool to room temperature and was filtered. The solid was washed with ethanol, air dried, and dried in vacuo (60° C.,<1 mm) to afford 3-amino-3-(3',4'-dimethoxyphenyl)propionic acid as a white solid, (100.14 grams, 56% yield), no further purification was carded out: mp 208.0°-210.0° C.; 1H NMR (D2 O/NaOD/TSP)δ7.08-6.91 (m, 3H), 4.22 (t, J=7 Hz, 1H), 3.87 (s, 3H), 3.83 (s, 3H), 2.55 (dd, J=2, 7Hz, 2H); 13C NMR(D2 O/NaOD/TSP)δ182.9, 150.8, 149.8, 140.7, 121.6, 114.6, 112.8, 58.6, 55.4, 49.8.

Workup

  1. temperaturewas heated to 45°-50° C.
  2. customresulting in an orange solution
  3. temperaturethe solution was refluxed overnight
  4. customA white solid precipitated
  5. temperatureon heating
  6. filtrationwas filtered
  7. washThe solid was washed with ethanol, air
  8. customdried
  9. customdried in vacuo (60° C.,<1 mm)

Sources & evidence

ORD record
ord-f279e23865634665aba0d3169dd382b9
Source dataset
uspto-grants-1997_12
Patent number
US05703098

Reaction notes

Loading…