Methyl iodide → 5-Bromo-1-methylpyridin-2(1H)-one

HRID 406663Notes

Reaction equation

HRID 406663 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7](=[O:10])[NH:8][CH:9]=1.[CH3:11]I>C1COCC1>[Br:3][C:4]1[CH:5]=[CH:6][C:7](=[O:10])[N:8]([CH3:11])[CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 5995285-Bromo-2-hydroxypyridine

Product 1

HCID 130240275-Bromo-1-methylpyridin-2(1H)-oneYield 96.78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of NaH (4.8 g, 0.2 mol) in THF (10 mL) was added a solution of 5-bromopyridin-2(1H)-one (8.6 g, 0.05 mol) in THF (120 mL) at 0° C. The resulting mixture was stirred for 1 h and CH3I (35.5 g, 0.25 mol) was added. The mixture was stirred for 3 h. The reaction was quenched with aqueous NH4Cl solution. The organic phase was concentrated to give the crude product, which was purified by column chromatography to give 5-bromo-1-methylpyridin-2(1H)-one (8.9 g, 96.78%). 1H NMR (CDCl3): δ=3.5 (S, 3H), 6.52 (m, 1H), 7.32 (m, 1H), 7.45(m, 1H).

Workup

  1. stirringThe mixture was stirred for 3 h
  2. customThe reaction was quenched with aqueous NH4Cl solution
  3. concentrationThe organic phase was concentrated
  4. customto give the crude product, which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-09d280c739e64da797d84ee2089e2ada
Source dataset
uspto-grants-2014_06
Patent number
US08754076B2

Reaction notes

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