Formic Acid → 2-Oxo-1,2,3,4-tetrahydroquinoline-5-carbaldehyde

HRID 503991Notes

Reaction equation

HRID 503991 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7](=[O:13])[NH:8]2)#N.C(O)=[O:15]>[Ni]>[O:13]=[C:7]1[CH2:6][CH2:5][C:4]2[C:3]([CH:1]=[O:15])=[CH:12][CH:11]=[CH:10][C:9]=2[NH:8]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 665969262-Oxo-1,2,3,4-tetrahydroquinoline-5-carbonitrile

Product 1

HCID 112753262-Oxo-1,2,3,4-tetrahydroquinoline-5-carbaldehydeYield 76%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst2×

Procedure

5-Cyano-3,4-dihydro-1H-quinolin-2-one (100 mg) and Raney nickel (100 mg) were suspended in formic acid (10 ml), and the suspension was heated under reflux for 2 hours. An additional 100 mg of Raney nickel was added, followed by heating under reflux for 1 hour. The reaction mixture was filtered to remove the insoluble matter, and the filtrate was concentrated. Ethyl acetate and water were added to the residue, and after stirring, the mixture was filtered through Celite. The filtrate was separated into layers, and the organic layer was washed with water and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was recrystallized from an ethyl acetate-n-hexane mixed solvent to thereby obtain 77 mg (yield: 76%) of 2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde as a light brown powder.

Workup

  1. temperaturethe suspension was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureby heating
  4. temperatureunder reflux for 1 hour
  5. filtrationThe reaction mixture was filtered
  6. customto remove the insoluble matter
  7. concentrationthe filtrate was concentrated
  8. additionEthyl acetate and water were added to the residue
  9. filtrationthe mixture was filtered through Celite
  10. customThe filtrate was separated into layers
  11. washthe organic layer was washed with water
  12. dry with materialdried over anhydrous sodium sulfate
  13. concentrationAfter concentration under reduced pressure
  14. customthe residue was recrystallized from an ethyl acetate-n-hexane mixed solvent

Sources & evidence

ORD record
ord-810bb6cc395c48898c13a3c5bb97025c
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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