Malonic Acid → 3-Amino-3-(5-bromopyridin-3-yl)propionic acid

HRID 526341Notes

Reaction equation

HRID 526341 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=O)[CH:5]=[N:6][CH:7]=1.[C:10]([OH:16])(=[O:15])[CH2:11]C(O)=O.C([O-])(=O)C.[NH4+:21]>C(O)C>[NH2:21][CH:8]([C:4]1[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[CH2:11][C:10]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 517165Ammonium AcetateHCID 27847345-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 212566853-Amino-3-(5-bromopyridin-3-yl)propionic acidYield 69.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

9.50 g (51.07 mmol) 5-bromopyridine-3-carbaldehyde were suspended in 22 ml ethanol. 5.31 g (51.07 mmol) propanedioic acid and 8.27 g (107.25 mmol) ammonium acetate were added. The mixture was refluxed for 4 hours and after cooling to room temperature filtrated. The residue was washed with cold ethanol and dried in vacuum at 45° C. to give 8.69 g (69%) 3-amino-3-(5-bromo-pyridin-3-yl)propionic acid.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. filtrationfiltrated
  3. washThe residue was washed with cold ethanol
  4. customdried in vacuum at 45° C.

Sources & evidence

ORD record
ord-017847f34f2946bdb7345f33526a0588
Source dataset
uspto-grants-2016_05
Patent number
US09345793B2

Reaction notes

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