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

HRID 1811400Notes

Reaction equation

HRID 1811400 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-d156ddef40f34810ae73ffdcb7ceedc8
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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