Methyl iodide → 5-(4-Bromophenyl)-1-methyl-2-pyrrolidinone

HRID 1988617Notes

Reaction equation

HRID 1988617 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[NH:12][C:11](=[O:13])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:16]I>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[N:12]([CH3:16])[C:11](=[O:13])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 120565955-(4-BROMOPHENYL)PYRROLIDIN-2-ONE

Product 1

HCID 577627945-(4-Bromophenyl)-1-methyl-2-pyrrolidinoneYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(4-bromophenyl)-2-pyrrolidinone (preparation described in WO00/21958) (200 mg, 0.83 mmol) in dimethylformamide (5 ml) was treated with a solid suspension of sodium hydride (60% in mineral oil, 35 mg, 0.88 mmol). The reaction mix was allowed to stir for 20 minutes, then methyl iodide (124 mg, 0.88 mmol) was added and the whole mix stirred for a further 18 hours. The reaction mixture was quenched with a few drops of water then partitioned between dichloromethane (15 ml), and water (60 ml), the organic layer was removed and washed with water again (2×10 ml), then reduced to minimum volume under reduced pressure to give the title compound as a brown oil (141 mg, 67%).

Workup

  1. additionThe reaction mix
  2. additionthe whole mix
  3. stirringstirred for a further 18 hours
  4. customThe reaction mixture was quenched with a few drops of water
  5. customthen partitioned between dichloromethane (15 ml), and water (60 ml)
  6. customthe organic layer was removed
  7. washwashed with water again (2×10 ml)

Sources & evidence

ORD record
ord-17a48ccbeb7e423cb586a60b37a37227
Source dataset
uspto-grants-2010_01
Patent number
US07642256B2

Reaction notes

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