Methyl iodide → HCID 19759483, compound

HRID 1586803Notes

Reaction equation

HRID 1586803 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.[CH3:15]I>C1C=CC=CC=1.[OH-].[Na+].[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:15][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 2

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

Product 1

HCID 19759483HCID 19759483, compoundYield 94.2%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 241BenzeneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 4-(4-methylphenyl)pyrrole-3-carbonitrile (2.0 g) in a mixture of benzene (40 ml) and 50% 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-279349b58d944a5bbbdc21fed8589fa7
Source dataset
uspto-grants-1993_06
Patent number
US05215994

Reaction notes

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