Reaktion #670465

Reaktionsgleichung

1-Methyl-3,4-dihydroisoquinoline

potassium nitrate

ammonium hydroxide

→

1-Methyl-7-nitro-3,4-dihydroisoquinoline

Lösungsmittel

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwith cooling
2. 2
   workup.ADDITIONpoured over ice
3. 3
   Sonstigethe precipitated solid was collected
4. 4
   Waschenwashed with water
5. 5
   Sonstigedried

Vorschrift

1-Methyl-3,4-dihydroisoquinoline (4.25 g, 29.3 mmol) was dissolved in ice cold concentrated sulfuric acid (15 ml) and to this was added potassium nitrate (3.25 g, 32.2 mmol) portionwise with cooling. The mixture was stirred overnight, poured over ice, basified with concentrated ammonium hydroxide, and the precipitated solid was collected, washed with water and dried: 4.47 g (80%), MS (M+H)+ 191, 1H NMR (D2O), 8.30 (d, 1H), 8.22 (dd, 1H), 7.39 (d, 1H), 3.80-3.62 (m, 2H), 2.92-2.70 (m, 2H), 2.48 (broad s, 3H).

Quelle