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

Participants

Reaction Steps

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).

Provenance & Evidence