Methyl iodide → 4',5'-Dimethoxy-2'-(methylamino)acetophenone

HRID 358712

Reaktionsgleichung

Reaktionsgleichung von HRID 358712
IC.[NH2:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[C:14](=[O:16])[CH3:15].[C:17](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:11][O:10][C:8]1[C:7]([O:12][CH3:13])=[CH:6][C:5]([C:14](=[O:16])[CH3:15])=[C:4]([NH:3][CH3:17])[CH:9]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 602085Ethanone, 1-(2-amino-4,5-dimethoxyphenyl)-

Produkt 1

HCID 679300644',5'-Dimethoxy-2'-(methylamino)acetophenone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Iodomethane (14 ml) was added to a stirred mixture of 2'-amino-4',5'-dimethoxyacetophenone (40 g), potassium carbonate (31.2 g) and dry dimethylformamide (200 ml) and the mixture stirred at ambient temperature for 40 hours. The solvent was evaporated under reduced pressure and the residue triturated with dichloromethane (250 ml). The mixture was filtered and the filter bed washed with dichloromethane (50 ml). The combined filtrate and washing were evaporated and the residue purified by flash chromatography on a silica gel column eluted with dichloromethane:industrial methylated spirit (99:1then 49:1) followed by trituration with diethyl ether (400 ml then 100 ml) to give the novel compound 4',5'-dimethoxy-2'-(methylamino)acetophenone, m.p. 121°-123.5°.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue triturated with dichloromethane (250 ml)
  3. filtrationThe mixture was filtered
  4. washthe filter bed washed with dichloromethane (50 ml)
  5. washThe combined filtrate and washing
  6. customwere evaporated
  7. customthe residue purified by flash chromatography on a silica gel column
  8. washeluted with dichloromethane:industrial methylated spirit (99:1then 49:1)

Quellen und Nachweise

ORD-Eintrag
ord-f19f726243cd464fb26f51ac0b0ebb3f
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US04997840

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