Methyl iodide → HCID 5302363, compound

HRID 1846737Notes

Reaction equation

HRID 1846737 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:10]=[CH:9][NH:8][CH:7]=1)([O-:5])=[O:4].I[CH3:12].[H][H]>CCCCCC.CN(C=O)C.CCOC(C)=O.O>[CH3:12][N:8]1[CH:9]=[CH:10][C:6]([N+:3]([O-:5])=[O:4])=[CH:7]1

Participants

9

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1458133-NitropyrroleHCID 178418361HCID 178418361, compound

Product 1

HCID 5302363HCID 5302363, compoundYield 87.8%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To sodium hydride (300 mg, 60% in mineral oil, 7.50 mmol) in a flask, which was washed with hexane twice, a solution of 3-nitropyrrole (500 mg, 4.46 mmol) and iodomethane (0.560 mL, 8.97 mmol) in DMF (4 mL) was added. Hydrogen gas evolved. The mixture was then stirred at room temperature for 20 h. Water and EtOAc were added. Organic phase was separated, washed with water, dried over Na2SO4, concentrated in vacuo to give 1-methyl-3-nitro-1H-pyrrole (494 mg).

Workup

  1. customOrganic phase was separated
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3002fa8035584e57b38c0414cf2e7b3a
Source dataset
uspto-grants-2015_02
Patent number
US08952027B2

Reaction notes

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