Réaction #738132

Équation de réaction

KOH

(±) 1-methyl-3,4-dihydroisoquinoline

potassium nitrate

→

title compound

Rendement 57.0%

(±) 1-Methyl-7-nitro-3,4-dihydroisoquinoline

Rendement 57.0%

Solvants

sulfuric acid

sulfuric acid

Conditions de réaction

Traitement

1. 1
   ExtractionExtraction into dichloromethane (3×50 ml)
2. 2
   Séchagedrying over anhydrous sodium sulfate and evaporation in vacuo
3. 3
   Autreyielded the crude product
4. 4
   AutrePurification by chromatography through silica gel
5. 5
   Lavageeluting with (0.5% 0.88 NH3: 4.5% CH3OH: 95% CH2Cl2)

Mode opératoire

A solution of (±) 1-methyl-3,4-dihydroisoquinoline (2.57 g, 17.7 mmol) in conc. sulfuric acid (10 ml) was added dropwise to a stirred mixture of potassium nitrate (1.93 g, 19.1 mmol) in conc. sulfuric acid (10 ml) at −5° C. The mixture was allowed to reach room temperature over 2 h and then heated at 60° C. for 4 h. The reaction mixture was poured into ice-water (100 ml) and basified (pH 9) with KOH pellets. Extraction into dichloromethane (3×50 ml), drying over anhydrous sodium sulfate and evaporation in vacuo yielded the crude product. Purification by chromatography through silica gel, eluting with (0.5% 0.88 NH3: 4.5% CH3OH: 95% CH2Cl2) afforded the title compound as a dark brown oil (1.92 g, 57%).

Source