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

Temperature

50 °C

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).

1. filtrationAfter the reaction mixture was filtrated by Celite
2. concentrationthe filtrate was concentrated under reduced pressure
3. additionTo the residue, a saturated aqueous NaHCO3 solution was added
4. filtrationfiltrated
5. customto obtain solid A
6. extractionThe filtrate was extracted three times with CHCl3
7. dry with materialthe combined organic layers were dried over Na2SO4
8. concentrationconcentrated under reduced pressure
9. additionsuspended in a solution mixture of EtOAc/CHCl3/acetone (10/10/1; v/v/v)
10. stirringthe mixture was stirred at room temperature for one hour
11. filtrationfiltrated

ORD record

ord-0cfd8b495ab54274b6fcc100e38e8a38

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08461182B2