Methanol → 4,6-Dimethoxy-1(2H)-isoquinolinone

HRID 2361607Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2361607
F[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][NH:8][C:9]2=[O:12])=[CH:4][C:3]=1[O:13][CH3:14].CS(O)(=O)=O.[CH3:20][OH:21]>>[CH3:20][O:21][C:6]1[C:5]2[C:10](=[CH:11][CH:2]=[C:3]([O:13][CH3:14])[CH:4]=2)[C:9](=[O:12])[NH:8][CH:7]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 6395Methanesulfonic AcidHCID 218898267-FLUORO-6-METHOXYISOQUINOLIN-1(2H)-ONE

Produkt 1

HCID 222502544,6-Dimethoxy-1(2H)-isoquinolinoneAusbeute 48,8 %

Versuchsvorschrift

To a solution of 7-fluoro-6-methoxyisoquinolin-1(2H)-one (7 g, 40.0 mmol) in methanol (70 ml) was added iodozobenzenediacetate (14.16 g, 40.0 mmol) followed by methane sulphonic acid (11.52 g, 120 mmol) at room temperature. The reaction mass was heated at reflux for 3 h. The solvent was evaporated and the residue was diluted with cold water. The precipitated solid was filtered, washed with water to get crude compound (4 g, 48.8%) as a light red colored solid. 1H NMR (400 MHz, DMSO): δ ppm 8.11-8.09 (d, J=8 Hz, 1H), 7.19 (s, 1H), 7.13-7.11 (d, J=8 Hz, 1H), 6.72-6.71 (d, J=12 Hz, 1H), 3.89 (s, 3H), 3.79 (s, 3H); MS: MS m/z 206.1 (M++1).

Aufarbeitung

  1. temperatureThe reaction mass was heated
  2. temperatureat reflux for 3 h
  3. customThe solvent was evaporated
  4. additionthe residue was diluted with cold water
  5. filtrationThe precipitated solid was filtered
  6. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-cfeef8655c4c4e28af080d389c217def
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691757B2

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