Ethyl bromoacetate → ethyl 2-(4-oxopyridin-1(4H)-yl)acetate

HRID 845386Notes

Reaction equation

HRID 845386 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](=[O:7])[CH2:3][CH:2]=1.Br[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:13]([O:12][C:10]([CH2:9][N:1]1[CH:2]=[CH:3][C:4](=[O:7])[CH:5]=[CH:6]1)=[O:11])[CH3:14]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 17984897Piridin-4-one

Product 1

HCID 12254000ethyl 2-(4-oxopyridin-1(4H)-yl)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

14.25 g of 4-pyridone was dissolved in 250 ml of DMF, and 25 ml of ethyl bromoacetate and 31.1 g of potassium carbonate were added thereto and reacted for 2.5 hours at 60° C. After the reaction, the insoluble part was filtrated out, and the remaining filtrate solution was concentrated. The formed residue was purified with silicagel-column chromatography (chloroform/methanol=10/1-5/1), to obtain 22.8 g of 1-ethoxycarbonylmethyl-4-pyridone. This was dissolved in 400 ml of dimethoxyethane and 30 g of Lawesson's reagent was added thereto and reacted for 30 minutes, while heated under reflux. After the reaction, the reaction solution was concentrated, and the residue formed was purified with silicagel-column chromatography (chloroform/methanol=20/1) and then crystallized with dichloromethane/ether, to obtain 13.6 g of 1-ethoxycarbonylmethyl-4-thiopyridone.

Workup

  1. customreacted for 2.5 hours at 60° C
  2. customAfter the reaction
  3. filtrationthe insoluble part was filtrated out
  4. concentrationthe remaining filtrate solution was concentrated
  5. customThe formed residue was purified with silicagel-column chromatography (chloroform/methanol=10/1-5/1)

Sources & evidence

ORD record
ord-870b3154f557431fbb73379f2922d2f7
Source dataset
uspto-grants-1988_07
Patent number
US04758557

Reaction notes

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