Methyl iodide → HCID 19759483, compound

HRID 248381Notes

Reaction equation

HRID 248381 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:13]#[N:14])=[CH:10][NH:11][CH:12]=2)=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:17]I>C1C=CC=CC=1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:17][N:11]1[CH:12]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)[C:9]([C:13]#[N:14])=[CH:10]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 136318634-(4-Methylphenyl)-1H-pyrrole-3-carbonitrile

Product 1

HCID 19759483HCID 19759483, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 241BenzeneSolvent

Procedure

To a solution of 4-(4-methylphenyl)pyrrole-3-carbonitrile (2.0 g) in a mixture of benzene (40 ml) and aqueous sodium hydroxide solution (10 ml) was added methyliodide (1.56 g) and tetrabutylammonium iodide (4.06 g) in that order in an ice bath. The mixture was stirred for 3 hours at ambient temperature and extracted twice with diethyl ether. The combined organic layers were washed with aqueous hydrochloric acid and then water, dried, and concentrated in vacuo to yield 1-methyl-4-(4-methylphenyl)pyrrole-3-carbonitrile (2.03 g) as pale yellow crystals.

Workup

  1. extractionextracted twice with diethyl ether
  2. washThe combined organic layers were washed with aqueous hydrochloric acid
  3. dry with materialwater, dried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c7f42dda4c649efa5c9e7dc89e0d202
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

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