Reaktion #366224

Reaktionsgleichung

2-allyloxy-4,7-dichloro-6-(pyrrolidin-1-yl)benzo[de]isoquinoline-1,3-dione

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title compound

Ausbeute 43.8%

4,7-Dichloro-2-hydroxy-6-(pyrrolidin-1-yl)benzo[de]isoquinoline-1,3-dione

Ausbeute 43.8%

Lösungsmittel

trifluoroacetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeevaporated in vacuo
2. 2
   workup.DISSOLUTIONredissolved in methanol which
3. 3
   Sonstigewas also evaporated
4. 4
   SonstigeThe residue was partitioned between dichloromethane/water
5. 5
   Sonstigeseparated
6. 6
   Sonstigethe organic layer dried
7. 7
   Sonstigeevaporated in vacuo
8. 8
   SonstigeThe residue was triturated with petroleum ether
9. 9
   Sonstigethe solid removed by filtration
10. 10
    Sonstigedried in vacuo

Vorschrift

A solution of 2-allyloxy-4,7-dichloro-6-(pyrrolidin-1-yl)benzo[de]isoquinoline-1,3-dione (0.5 g, 1.3 mmol, from Example J4) in trifluoroacetic acid (10 mL) was treated with boron tristrifluoroacetate (6 mL, 6.0 mmol, 1.0 M in trifluoroacetic acid). The reaction mixture was stirred at room temperature for 4 hours and evaporated in vacuo. The residue was chased with dichloro methane and redissolved in methanol which was also evaporated. The residue was partitioned between dichloromethane/water, separated, the organic layer dried, and evaporated in vacuo. The residue was triturated with petroleum ether, the solid removed by filtration, and dried in vacuo to give 0.2 g of the title compound, mp 243-245° C.

Quelle