Formic Acid → 1,2,3,4-Tetrahydro-2-oxo-7-quinolinecarboxaldehyde

Participants

Reaction Conditions

Reaction Steps

To a formic acid (250 mL) solution of the compound (32.6 g) obtained in Step 1-3, Raney nickel catalyst (50.0 g) was added and the mixture was stirred at 50° C. for 2 hours. After the reaction mixture was filtrated by Celite, the filtrate was concentrated under reduced pressure. To the residue, a saturated aqueous NaHCO3 solution was added and the mixture was adjusted to pH 6 and filtrated to obtain solid A. The filtrate was extracted three times with CHCl3 and the combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The residue and solid A were combined and suspended in a solution mixture of EtOAc/CHCl3/acetone (10/10/1; v/v/v) and the mixture was stirred at room temperature for one hour and filtrated to obtain 2-oxo-1,2,3,4-tetrahydroquinoline-7-carbaldehyde (19.8 g, a light yellow solid).

Provenance & Evidence