Reaktion #2448780

Reaktionsgleichung

1-chloroisoquinolin-4-ol

TMS-diazomethane

→

1-chloro-4-methoxyisoquinoline

Ausbeute 46.4%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto come to room temperature
2. 2
   SonstigeSolvent was evaporated under reduced pressure
3. 3
   Sonstigeto get crude compound
4. 4
   SonstigeThe crude compound was purified by silica gel chromatography

Vorschrift

To a solution of 1-chloroisoquinolin-4-ol (5.0 g, 27.8 mmol) in acetonitrile (50 mL) was added TMS-diazomethane (12.73 g, 111.2 mmol) at 0° C. The reaction mixture was allowed to come to room temperature and stirred for 2 h. Solvent was evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get 1-chloro-4-methoxyisoquinoline (2.5 g, 46.4%) as off-white solid. 1H NMR (400 MHz, CD3OD): δ ppm 8.29-8.17 (m, 2H), 7.97 (s, 1H), 7.91-7.82 (m, 2H), 4.05 (s, 3H); MS: MS m/z 194.7 (M++1).

Quelle