Malonic Acid → HCID 71258954, compound

HRID 526354Notes

Reaction equation

HRID 526354 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([CH:10]=O)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:12]([OH:18])(=[O:17])[CH2:13]C(O)=O.C([O-])(=O)C.[NH4+:23]>C(O)C>[NH2:23][CH:10]([C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=1)[CH2:13][C:12]([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 517165Ammonium AcetateHCID 112173392-Fluoro-4-formylbenzonitrile

Product 1

HCID 71258954HCID 71258954, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

500 mg (3.35 mmol) 2-fluoro-4-formylbenzonitrile were suspended in 2 ml ethanol. 349 mg (3.35 mmol) propanedioic acid and 0.54 g (7.04 mmol) ammonium acetate were added. The mixture was refluxed for 6 hours and after cooling filtrated. The residue was washed with ethanol and dried in vacuum to give 360 mg (52%) 3-amino-3-(4-cyano-3-fluorophenyl) propionic acid.

Workup

  1. temperatureThe mixture was refluxed for 6 hours
  2. temperatureafter cooling
  3. filtrationfiltrated
  4. washThe residue was washed with ethanol
  5. customdried in vacuum

Sources & evidence

ORD record
ord-3bf9bba15a4946d8aeaab27e11df5690
Source dataset
uspto-grants-2016_05
Patent number
US09345793B2

Reaction notes

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