Water → Ethyl 1-benzoyl-3,5-dimethyl-2-oxo-1,2-dihydropyridine-4-carboxylate

HRID 1501280Notes

Reaction equation

HRID 1501280 reaction equation
[Br-].[CH2:2]([O:4][C:5]([C:7]1[C:12]([CH3:13])=[CH:11][N+:10]([CH:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)C)=[CH:9][C:8]=1[CH3:22])=[O:6])[CH3:3].[OH-:23].[Na+].[OH2:25]>[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[C:14]([N:10]1[CH:11]=[C:12]([CH3:13])[C:7]([C:5]([O:4][CH2:2][CH3:3])=[O:6])=[C:8]([CH3:22])[C:9]1=[O:25])(=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 131734281HCID 131734281, compound

Product 1

HCID 89585151Ethyl 1-benzoyl-3,5-dimethyl-2-oxo-1,2-dihydropyridine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 178511488HCID 178511488, compoundCatalyst

Procedure

To the solution of 4-(ethoxycarbonyl)-3,5-dimethyl-1-(1-phenylethyl)pyridin-1-ium bromide (3.91 mmol) was added portionwise the mixture of potassium ferricyanide (2.57 g, 7.81 mmol) and sodium hydroxide (0.94 g, 23.44 mmol) in H2O (5 ml) for 2 h at room temperature. The solution was concentrated under vacuum, diluted with water and extracted with ethyl acetate. The organic layers were combined, dried over Na2SO4 and concentrated to give a residue. The residue was used to the next step without further purification.

Workup

  1. concentrationThe solution was concentrated under vacuum
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give a residue
  7. customThe residue was used to the next step without further purification

Sources & evidence

ORD record
ord-d1820e629b0445cd91855ddb4b881227
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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