Methyl iodide → HCID 20222400, compound

HRID 980299Notes

Reaction equation

HRID 980299 reaction equation
[CH3:1]I.[Mg].[Br:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]2[CH:14]=[CH:15][N+:16]([O-:18])=[O:17].[Cl-].[NH4+]>CCOCC.O1CCCC1>[Br:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]2[CH:14]([CH3:1])[CH2:15][N+:16]([O-:18])=[O:17]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 8889955-bromo-3-(2-nitroethenyl)-1H-indoleHCID 5462224Magnesium

Product 1

HCID 20222400HCID 20222400, compoundYield 49.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl iodide (35.5 g) was added to a stirred suspension of magnesium (4.8 g) in dry ether (100 ml) over a period of 10 min. To the grey solution was added a solution of 5-bromo-3-(2-nitroethenyl)-1H-indole (13.4 g) in dry tetrahydrofuran (250 ml) over a period of 11/2 h. The resulting mass was stirred vigorously for 12 h, followed by the careful addition of saturated ammonium chloride (250 ml). After separation of the organic phase, the aqueous phase was extracted with ether (500 ml). The combined organic extracts were successively washed with 5% sodium sulphite solution (500 ml) and water (500 ml). Evaporation of the dried (MgSO4) ethereal phase gave a brown oil which was chromatographed on Kieselgel 60 using diethyl ether as eluant to give the title compound as a yellow gum (7.03 g) T.L.C. silica/diethyl ether Rf 0.5.

Workup

  1. customAfter separation of the organic phase
  2. extractionthe aqueous phase was extracted with ether (500 ml)
  3. washThe combined organic extracts were successively washed with 5% sodium sulphite solution (500 ml) and water (500 ml)
  4. customEvaporation of the
  5. dry with materialdried (MgSO4) ethereal phase
  6. customgave a brown oil which
  7. customwas chromatographed on Kieselgel 60 using diethyl ether as eluant

Sources & evidence

ORD record
ord-0ad368cf003746a694b07480566f6564
Source dataset
uspto-grants-1987_01
Patent number
US04636521

Reaction notes

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