Malonic Acid → 3-amino-3-(3-methylphenyl)propanoic acid

HRID 1371531Notes

Reaction equation

HRID 1371531 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[C:10]([OH:16])(=[O:15])[CH2:11]C(O)=O.C([O-])(=O)C.[NH4+:21]>COCCO>[NH2:21][CH:5]([C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([CH3:1])[CH:3]=1)[CH2:11][C:10]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 121053-MethylbenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 27642983-amino-3-(3-methylphenyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
80 °C

Procedure

11.8 ml of 3-methylbenzaldehyde are added to a mixture of 10.4 g of malonic acid and 15.4 g of ammonium acetate in 150 ml of 2-methoxyethanol, and the mixture is heated overnight at 80° C. After cooling to RT, the precipitate formed is filtered off under suction, washed with ether and dried. 6.8 g of the expected product are obtained.

Workup

  1. temperatureAfter cooling to RT
  2. customthe precipitate formed
  3. filtrationis filtered off under suction
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-5a501653de8a4fa78aac7f124847d97a
Source dataset
uspto-grants-2007_01
Patent number
US07157454B2

Reaction notes

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