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Malonic Acid → 3-amino-3-(2,4-dimethoxyphenyl)propanoic Acid

HRID 1079299
Notes
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Reaction equation

HRID 1079299 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[C:13]([OH:19])(=[O:18])[CH2:14]C(O)=O.C([O-])(=O)C.[NH4+:24]>C(O)C>[NH2:24][CH:5]([C:4]1[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:3]=1[O:2][CH3:1])[CH2:14][C:13]([OH:19])=[O:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 691752,4-DimethoxybenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 99214293-amino-3-(2,4-dimethoxyphenyl)propanoic AcidYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 2,4-dimethoxybenzaldehyde (21 g, 0.126 mol), malonic acid (20 g, 0.192 mol), ammonium acetate (30 g, 0.39 mol) and ethanol (40 ml) was stirred and heated on a water bath. After refluxing for 4 h the mixture was cooled to 40° C. and the precipitated salt was filtered off and washed with cold ethanol (40 ml). By additional cooling on ice a further crystalline material precipitated, which was isolated and washed with cold ethanol (40 ml) and ether (40 ml). Recrystallisation from ethanol/water 60:40 gave 3-amino-3-(2,4-dimethoxyphenyl)propanoic acid (10.3 g, 38%).

Workup

  1. temperatureheated on a water bath
  2. temperatureAfter refluxing for 4 h the mixture
  3. filtrationthe precipitated salt was filtered off
  4. washwashed with cold ethanol (40 ml)
  5. temperatureBy additional cooling on ice a further crystalline material
  6. customprecipitated
  7. customwhich was isolated
  8. washwashed with cold ethanol (40 ml) and ether (40 ml)
  9. customRecrystallisation from ethanol/water 60:40

Sources & evidence

ORD record
ord-cb229fddf24347dc9a95aaaa3c52f191
Source dataset
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05580751

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes