Malonic Acid → 3-AMINO-3-CYCLOPROPYLPROPANOIC ACID

HRID 2377095Notes

Reaction equation

HRID 2377095 reaction equation
[CH:1]1([CH:4]=O)[CH2:3][CH2:2]1.[C:6]([O-:9])(=[O:8])[CH3:7].[NH4+:10].C(O)(=O)CC(O)=O>C(O)C>[NH2:10][CH:4]([CH:1]1[CH2:2][CH2:3]1)[CH2:7][C:6]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 123114CyclopropanecarboxaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 101540633-AMINO-3-CYCLOPROPYLPROPANOIC ACIDYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of cyclopropanecarboxaldehyde (150.2 g, 2.1 mol), ammonium acetate (329.9 g, 4.3 mol), malonic acid (223 g, 2.1 mol), and ethanol (850 mL) was stirred at reflux for 19 h. The reaction was analyzed by LCMS and determined to be complete. The mixture was allowed to cool to room temperature. The heterogeneous mixture was further cooled with an ice-bath and stirred 3 h prior to collecting the solid precipitate by suction filtration. The cake was washed with cold ethanol (displacement wash: 250 mL) and the solids dried under vacuum to provide 146.5 g of the desired compound (53% yield) as a white solid. mp: 206-208° C.

Workup

  1. temperatureat reflux for 19 h
  2. temperatureThe heterogeneous mixture was further cooled with an ice-bath
  3. stirringstirred 3 h
  4. customto collecting the solid precipitate
  5. filtrationby suction filtration
  6. washThe cake was washed with cold ethanol (displacement wash: 250 mL)
  7. customthe solids dried under vacuum

Sources & evidence

ORD record
ord-f2ef3fd474ef44aa82b1e977994a12a9
Source dataset
uspto-grants-2008_12
Patent number
US07468375B2

Reaction notes

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