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

HRID 850602Notes

Reaction equation

HRID 850602 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 4-1 (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 4-2 as a white solid (3.84 g, 17.8 mmol, 56%). 1H NMR (300 MHz, D2O):δ 8.91 (d, J=2 Hz 1H), 8.21 (d, J=2 Hz, 1H), 8.12 (d, J=8 Hz, 1H), 7.84 (d, J=7 Hz, 1H), 7.72 (t, J=7 Hz, H), 7.54 (t, J=7 Hz, 1,H), 4.72 (m, 1H), 2.73 (m, 2H).

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-079fcbb5a37c4d1fbd544804ca9f4c28
Source dataset
uspto-grants-2000_01
Patent number
US06017926

Reaction notes

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