Formic Acid → HCID 86613922, compound

HRID 504005Notes

Reaction equation

HRID 504005 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7](=[O:14])[NH:8]2)#N.C(O)=[O:16]>[Ni]>[CH3:13][C:10]1[C:9]2[NH:8][C:7](=[O:14])[CH2:6][CH2:5][C:4]=2[C:3]([CH:1]=[O:16])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 66596859HCID 66596859, compound

Product 1

HCID 86613922HCID 86613922, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

5-Cyano-8-methyl-3,4-dihydro-1H-quinolin-2-one (2.0 g) and Raney nickel (10 g) were suspended in formic acid (40 ml), and the suspension was heated under reflux for 6 hours. 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-diethyl ether mixed solvent to thereby obtain 1.29 g (yield: 62%) of 8-methyl-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde as a light brown powder.

Workup

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

Sources & evidence

ORD record
ord-aa4a25629db2468ea69429b22ceefaa2
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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