Methyl iodide → HCID 19759522, compound

HRID 248393Notes

Reaction equation

HRID 248393 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([C:16]#[N:17])=[CH:13][NH:14][CH:15]=2)=[CH:7][CH:6]=1)=[O:4].[H-].[Na+].I[CH3:21]>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:12]([C:16]#[N:17])=[CH:13][N:14]([CH3:21])[CH:15]=2)=[CH:9][CH:10]=1)=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19759337HCID 19759337, compound

Product 1

HCID 19759522HCID 19759522, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-(4-methoxycarbonylphenyl)-1H-pyrrole-3-carbonitrile (3.00 g) in N,N-dimethylformamide (25 ml) was added sodium hydride (60% oil dispersion : 559 mg) at ambient temperature and the stirring was continued for half an hour at the same temperature. Iodomethane (1.99 g) was added to the mixture, and was stirred at ambient temperature for two hours. The reaction mixture was poured onto ice water and extracted with ethyl acetate and washed with 7% aqueous hydrochloric acid. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was recrystallized from ethanol to give 4-(4-methoxycarbonylphenyl)-1-methylpyrrole-3-carbonitrile (2.78 g) as pale yellow needles.

Workup

  1. waitthe stirring was continued for half an hour at the same temperature
  2. additionThe reaction mixture was poured onto ice water
  3. extractionextracted with ethyl acetate
  4. washwashed with 7% aqueous hydrochloric acid
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-4a7020f9441c4800a2ce68589eaa3045
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

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