Acetic Acid → HCID 66597026, compound

HRID 504001Notes

Reaction equation

HRID 504001 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([CH:13]=O)=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7](=[O:15])[NH:8]2.C(O)(=O)C>[C].[Pd].C(O)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7](=[O:15])[NH:8]2

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86233763882023-34-9

Product 1

HCID 66597026HCID 66597026, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

5-Methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-8-carboxaldehyde (1.00 g) and 10% palladium carbon (100 mg) were added to a mixed solvent of acetic acid (10 ml) and ethanol (10 ml), followed by catalytic reduction at 50° C. for 1 hour. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was subjected to extraction with ethyl acetate, and the extract was washed twice with water, washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was recrystallized from an ethyl acetate-diethyl ether mixed solvent to thereby obtain 826 mg (yield: 89%) of 5-methoxy-8-methyl-3,4-dihydro-1H-quinolin-2-one as a white powder.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. extractionThe residue was subjected to extraction with ethyl acetate
  4. washthe extract was washed twice with water
  5. washwashed with a saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was recrystallized from an ethyl acetate-diethyl ether mixed solvent

Sources & evidence

ORD record
ord-d18cc452ed7743c6beec6dba67cac9c5
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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