Malonic Acid → 3-(Quinolin-3-yl)propanoic acid

HRID 1108396Notes

Reaction equation

HRID 1108396 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(O)(=O)[CH2:14][C:15]([OH:17])=[O:16].C([O-])(=O)C.[NH4+]>C(O)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH2:11][CH2:14][C:15]([OH:17])=[O:16])[CH:2]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 836413-QuinolinecarboxaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 124157513-(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-b7b3baa5d58343398cb5dd2e39f4565b
Source dataset
uspto-grants-2000_05
Patent number
US06066648

Reaction notes

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