Ethanol → Methyl 2-oxo-6-phenyl-1,2-dihydropyridine-4-carboxylate

HRID 1096957Notes

Reaction equation

HRID 1096957 reaction equation
CCO.[C:4]1([C:10]2[CH:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[C:12]([O:20]CC3C=CC=CC=3)[N:11]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H][H]>[C].[Pd].C1COCC1>[O:20]=[C:12]1[CH:13]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:15]=[C:10]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:11]1

Participants

6

Reactant 3

HCID 702EthanolHCID 57930997Methyl 2-(benzyloxy)-6-phenylisonicotinateHCID 178418361HCID 178418361, compound

Product 1

HCID 57931020Methyl 2-oxo-6-phenyl-1,2-dihydropyridine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a nitrogen atmosphere, 10% palladium-carbon (3.2 g) was added to an EtOH (50 mL)-THF (5 mL) mixed solution of methyl 2-phenyl-6-benzyloxypyridine-4-carboxylate (5.3 g), and in a hydrogen atmosphere, this was stirred at room temperature for 9 hours. The reaction liquid was filtered through Celite, concentrated under reduced pressure, and a mixed solution of hexane/ethyl acetate=2/1 was added thereto. The precipitate was taken out through filtration, washed with that solution, and dried to obtain the title compound as a white powder. The filtrate was concentrated, and the residue was purified through silica gel column chromatography (from hexane/ethyl acetate to chloroform/methanol), and combined with the previous powder to obtain the title compound as a white powder.

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered through Celite
  3. concentrationconcentrated under reduced pressure
  4. additiona mixed solution of hexane/ethyl acetate=2/1 was added
  5. filtrationThe precipitate was taken out through filtration
  6. washwashed with that solution
  7. customdried

Sources & evidence

ORD record
ord-63dba7c81586406ba9868bfb410f9916
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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