Methanol → 7-Fluoro-4-methoxyisoquinolin-1-OL

HRID 1852216Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1852216
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.CS(O)(=O)=O.[CH3:18][OH:19]>>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:19][CH3:18])=[CH:7][NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 6395Methanesulfonic AcidHCID 222501227-Fluoro-1,2-dihydroisoquinolin-1-one

Produkt 1

HCID 222502317-Fluoro-4-methoxyisoquinolin-1-OLAusbeute 84 %

Versuchsvorschrift

To a solution of 7-fluoroisoquinolin-1(2H)-one (11 g, 67.4 mmol) in methanol was added iodozobenzenediacetate (21.7 g, 67.4 mmol) followed by methane sulphonic acid (7.78 g, 81 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 and washed with water to get crude compound (11 g, 84%) as light red color solid. 1H NMR (400 MHz, CD3OD): δ ppm 8.06-8.04 (m, 1H), 7.96-7.93 (m, 1H), 7.62-7.54 (m, 2H), 6.74 (s, 1H), 3.89 (s, 3H); MS: MS m/z 194.1 (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-fe286dd974444eccad29fbf2aa887c13
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957203B2

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