Methyl Acrylate → Methyl 3-(5-bromo-4-methyl-2-oxopyridin-1(2H)-yl)propanoate

HRID 588762Notes

Reaction equation

HRID 588762 reaction equation
[Br:1][C:2]1[C:3]([CH3:9])=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[C:16]([O:20][CH3:21])(=[O:19])[CH:17]=[CH2:18]>CN(C=O)C>[Br:1][C:2]1[C:3]([CH3:9])=[CH:4][C:5](=[O:8])[N:6]([CH2:18][CH2:17][C:16]([O:20][CH3:21])=[O:19])[CH:7]=1

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 11430Potassium CarbonateHCID 8199375-Bromo-2-hydroxy-4-methylpyridine

Product 1

HCID 117607153Methyl 3-(5-bromo-4-methyl-2-oxopyridin-1(2H)-yl)propanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-bromo-4-methylpyridin-2(1H)-one (1.0 g, 5.3 mmol) in DMF (10 mL), K2CO3 (1.5 g, 10.6 mmol) was added, followed by addition of methyl acrylate (0.91 g, 10.6 mmol) at 80° C. The mixture was stirred at 80° C. for 1 h. The mixture was allowed to cool to room temperature and then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was used directly in the next step without further purification.

Workup

  1. temperatureto cool to room temperature
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was used directly in the next step without further purification

Sources & evidence

ORD record
ord-4cb5cb7a243e4d8da8670d7428aa647d
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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