Réaction #792232

Équation de réaction

6-chloroisoquinoline-1,3(2H,4H)-dione

selenium dioxide

→

6-chloroisoquinoline-1,3,4(2H)-trione

Rendement 26.9%

Solvants

1,4-dioxane

Conditions de réaction

Traitement

1. 1
   Concentrationthe reaction mixture was concentrated under reduced pressure
2. 2
   AutrePurification of the residue

Mode opératoire

Under argon, a mixture of 6-chloroisoquinoline-1,3(2H,4H)-dione (600 mg g, 3.0 mmol) and selenium dioxide (357 mg, 3.2 mmol) in abs. 1,4-dioxane (20 ml) was stirred at a temperature of 100° C. for 3 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Purification of the residue that remained by column chromatography (gradient ethyl acetate/n-heptane) gave 6-chloroisoquinoline-1,3,4(2H)-trione (169 mg, 22% of theory) in the form of a slightly yellowish solid. 1H-NMR (400 MHz, d6-DMSO δ, ppm) 12.02 (br. s, 1H, NH), 8.12 (d, 1H), 8.01-7.95 (m, 2H).

Source