Methyl iodide → 3-Bromo-1-methyl-1,2-dihydropyridin-2-one

HRID 389667Notes

Reaction equation

HRID 389667 reaction equation
[Br:1][C:2]1[C:3]([OH:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH3:11]I>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[C:3](=[O:8])[N:4]([CH3:11])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178517701HCID 178517701, compound

Product 1

HCID 130240253-Bromo-1-methyl-1,2-dihydropyridin-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-bromo-pyridin-2-ol (10 g, 57.47 mmol) in DMF (100 ml) at 0° C. was added NaH (60%, 2.52 g, 63.22 mmol) portionwise under argon. After 30 min methyl iodide (4.29 ml, 68.97 mmol) was added dropwise and the reaction mixture was stirred for 15 h at RT. The mixture was diluted with ethyl acetate (100 ml), washed with water (2×200 ml) and brine (100 ml), dried over Na2SO4, and evaporated under reduced pressure. The crude product was used without further purification in step 21.5).

Workup

  1. washwashed with water (2×200 ml) and brine (100 ml)
  2. dry with materialdried over Na2SO4
  3. customevaporated under reduced pressure
  4. customThe crude product was used without further purification in step 21.5)

Sources & evidence

ORD record
ord-cc017c8edf8b434d88e70efb2c5a9dc2
Source dataset
uspto-grants-2013_02
Patent number
US08378092B2

Reaction notes

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