Methyl iodide → 3,5-Dimethoxy-N-methylbenzenamine

HRID 351117Notes

Reaction equation

HRID 351117 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[NH2:6].IC.[C:14]([O-])(=O)C.[Na+]>C1COCC1>[CH3:11][O:10][C:8]1[CH:7]=[C:5]([NH:6][CH3:14])[CH:4]=[C:3]([O:2][CH3:1])[CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 663013,5-DimethoxyanilineHCID 517045Sodium Acetate

Product 1

HCID 145235363,5-Dimethoxy-N-methylbenzenamineYield 29.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3,5-dimethoxyaniline (13.8 g, 90 mmol), Iodomethane (12.7 g, 90 mmol), and sodium acetate (7.4 g, 90 mmol) in 100 ml of anhydrous THF was stirred under nitrogen atmosphere for 10 hr. Then, THF was removed by rotary evaporation. The crude product was partitioned between water and ethyl ether. The ethereal extraction was separated and washed with water, brine, and dried over Na2SO4. Filtration and removal of solvent provided 13.6 g of crude product. The crude product was chromatographed on silica gel (33% acetone-petroleum ether) to afford the expected product 4.5 g (27% yield).

Workup

  1. customThen, THF was removed by rotary evaporation
  2. customThe crude product was partitioned between water and ethyl ether
  3. extractionThe ethereal extraction
  4. customwas separated
  5. washwashed with water, brine
  6. dry with materialdried over Na2SO4
  7. filtrationFiltration and removal of solvent
  8. customprovided 13.6 g of crude product
  9. customThe crude product was chromatographed on silica gel (33% acetone-petroleum ether)

Sources & evidence

ORD record
ord-0736f5026ca84458909cfdd1c9391405
Source dataset
uspto-grants-2007_02
Patent number
US07183313B2

Reaction notes

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