Réaction #457164

Équation de réaction

1-Methyl-3,4-dihydroisoquinoline

potassium nitrate

ammonium hydroxide

→

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

Solvants

Conditions de réaction

Traitement

1. 1
   Températurewith cooling
2. 2
   workup.ADDITIONpoured over ice
3. 3
   Autrethe precipitated solid was collected
4. 4
   Lavagewashed with water
5. 5
   Autredried

Mode opératoire

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).

Source