Malonic Acid → 3-Amino-3-(2-nitrophenyl)propionic acid

HRID 1368905Notes

Reaction equation

HRID 1368905 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[C:12]([OH:18])(=[O:17])[CH2:13]C(O)=O.C([O-])(=O)C.[NH4+:23]>C(O)C>[NH2:23][CH:6]([C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])[CH2:13][C:12]([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 111012-NitrobenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 27792173-Amino-3-(2-nitrophenyl)propionic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.06 mol of 2-nitrobenzaldehyde, 5.72 g of malonic acid, 8.5 g of ammonium acetate and 40 ml of ethanol are boiled under reflux for 8 hours and stirred at room temperature overnight. The cooled reaction mixture is then filtered with suction, washed with ethanol and ether and dried in air. 3-Amino-3-(2-nitrophenyl)propionic acid is obtained, melting point 222°. Subsequent esterification by activation with thionyl chloride and reaction with methanol under standard conditions produces methyl 3-amino-3-(2-nitrophenyl)propionate.

Workup

  1. temperatureunder reflux for 8 hours
  2. customThe cooled reaction mixture
  3. filtrationis then filtered with suction
  4. washwashed with ethanol and ether
  5. customdried in air

Sources & evidence

ORD record
ord-23ad35780f1c4f41a50756cd62ee7743
Source dataset
uspto-grants-2003_06
Patent number
US06576637B1

Reaction notes

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