Malonic Acid → 3-Amino-3-(pyridin-3-yl)propanoic acid

HRID 1490030Notes

Reaction equation

HRID 1490030 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.[C:9]([O-:12])(=[O:11])[CH3:10].[NH4+:13].C(O)(=O)CC(O)=O>CC(O)C>[NH2:13][CH:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[CH2:10][C:9]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 103713-PyridinecarboxaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 36065473-Amino-3-(pyridin-3-yl)propanoic acid

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To 300 ml of 3-pyridine carboxaldehyde in 3 liters of 2-propanol was added 297 g of ammonium acetate followed by 398 g of malonic acid. The reaction mixture was stirred at reflux for 5 hours. The precipitate was filtered while hot and washed with 2 liters of hot isopropanol. The resulting white solid was then dried to yield 220 g of DL-3-amino-3-(3-pyridyl)propionic acid as a white solid.

Workup

  1. temperatureat reflux for 5 hours
  2. filtrationThe precipitate was filtered while hot and
  3. washwashed with 2 liters of hot isopropanol
  4. customThe resulting white solid was then dried

Sources & evidence

ORD record
ord-6440f7176d2943a8a31d06b57295f214
Source dataset
uspto-grants-1997_10
Patent number
US05681820

Reaction notes

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