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

HRID 1004240Notes

Reaction equation

HRID 1004240 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH:11]=O)[CH:2]=1.[C:13]([OH:19])(=[O:18])[CH2:14]C(O)=O.C([O-])(=O)C.[NH4+:24]>C(O)C>[NH2:24][CH:11]([C:3]1[CH:2]=[N:1][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:14][C:13]([OH:19])=[O:18]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 836413-QuinolinecarboxaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 99425843-Amino-3-(quinolin-3-yl)propanoic acidYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution containing quinoline-3-carboxaldehyde 5-1 (5 g, 31.8 mmol), malonic acid (3.6 g, 35.0 mmol), and ammonium acetate (5.0 g, 63.6 mmol) in anhydrous ethanol (125 mL) was heated at reflux for 12 h. After cooling to room temperature, the resulting white solid was collected by filtration and washed with cold ethanol (150 mL) and then dried under vacuum to provide 5-2 as a white solid (3.84 g, 17.8 mmol, 56%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 12 h
  3. filtrationthe resulting white solid was collected by filtration
  4. washwashed with cold ethanol (150 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-aa80a60bf6384de795f2743b15f7ddff
Source dataset
uspto-grants-2000_04
Patent number
US06048861

Reaction notes

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