Ethyl bromoacetate → (3-Methyl-2-oxo-2H-pyridin-1-yl)-acetic acid ethyl ester

HRID 1786230Notes

Reaction equation

HRID 1786230 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][N:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]1=[O:1])[CH3:15]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 178426317HCID 178426317, compound

Product 1

HCID 22943407(3-Methyl-2-oxo-2H-pyridin-1-yl)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-hydroxy-3-methyl-pyridine (4.1 g, 37 mmol), ethyl bromoacetate (5.9 g, 35 mmol) and potassium carbonate (4.9 g, 35 mmol) in DMF (60 ml) was stirred at rt for 16 h. After evaporation of the solvent and extractive workup (ethyl acetate/water) the organic phase was concentrated and chromatographed (SiO2, heptane:ethyl acetate=100:0 to 40:60). The title compound elutes as the second product and was isolated as a colorless liquid (6.1g, 84%). MS: m/e=196.0[M+H]+.

Workup

  1. customAfter evaporation of the solvent and extractive workup (ethyl acetate/water) the organic phase
  2. concentrationwas concentrated
  3. customchromatographed (SiO2, heptane:ethyl acetate=100:0 to 40:60)

Sources & evidence

ORD record
ord-240c2c563c7543ad9d8e9928e954eff1
Source dataset
uspto-grants-2009_03
Patent number
US07507729B2

Reaction notes

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