Réaction #646657

Équation de réaction

sodium hydroxide

1,3-Dimethylisoquinoline

potassium nitrate

→

title compound

1,3-Dimethyl-5-nitroisoquinoline

Solvants

sulfuric acid

sulfuric acid

Conditions de réaction

Traitement

1. 1
   Températuremaintaining the temperature below 4° C
2. 2
   workup.ADDITIONAfter complete addition the solution
3. 3
   Extractionextracted with DCM
4. 4
   LavageThe extract was washed with brine
5. 5
   Autredried
6. 6
   Concentrationconcentrated to a yellow solid
7. 7
   AutrePurification by silica gel chromatography

Mode opératoire

1,3-Dimethylisoquinoline [(Chem. Lett., 1983, p. 791), 2.39 g, 15.20 mM], in concentrated sulfuric acid, (15 ml), was cooled to <4° C. A solution of potassium nitrate, (1.69 g, 16.72 mM), in concentrated sulfuric acid was added dropwise, maintaining the temperature below 4° C. After complete addition the solution was stirred at this temperature for a further 2 h then warmed to room temperature for 1 h. The reaction mixture was poured into ice water and the solution basified with sodium hydroxide and extracted with DCM. The extract was washed with brine, dried and concentrated to a yellow solid. Purification by silica gel chromatography afforded the title compound as a yellow crystalline solid.

Source