Potassium Nitrate → 5-Bromo-8-nitroisoquinoline

HRID 641922

Reaktionsgleichung

Reaktionsgleichung von HRID 641922
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[N+:12]([O-])([O-:14])=[O:13].[K+]>OS(O)(=O)=O>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2

Komponenten

4

Edukt 2

HCID 24434Potassium NitrateHCID 7364875-Bromoisoquinoline

Produkt 1

HCID 8169835-Bromo-8-nitroisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Into a 500 mL 3-necked round bottom flask was placed a solution of 5-bromoisoquinoline (22.24 g, 106.87 mmol) in H2SO4 (120 mL). This was followed by the addition of a solution of KNO3 (15.1 g, 149.36 mmol) in H2SO4 (100 mL), which was added dropwise with stirring, while cooling to a temperature of 20° C. over a time period of 1 hour. The resulting solution was allowed to react, with stirring, for 1 hour while the temperature was maintained at room temperature. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:5). The reaction mixture was then quenched by the adding 600 mL of H2O/ice. Adjustment of the pH to 8-10 was accomplished by the addition of NH3. H2O (30%). A filtration was performed. The filter cake was washed 2 times with 500 mL of H2O. The solid was dried in an oven under reduced pressure. This resulted in 25.59 g (90%) of 5-bromo-8-nitroisoquinoline as a yellow solid.

Aufarbeitung

  1. customInto a 500 mL 3-necked round bottom flask was placed
  2. additionwas added dropwise
  3. customto react
  4. stirringwith stirring, for 1 hour while the temperature
  5. temperaturewas maintained at room temperature
  6. customThe reaction mixture was then quenched by the adding 600 mL of H2O/ice
  7. additionAdjustment of the pH to 8-10 was accomplished by the addition of NH3
  8. filtrationA filtration
  9. washThe filter cake was washed 2 times with 500 mL of H2O
  10. customThe solid was dried in an oven under reduced pressure
  11. customThis resulted in 25.59 g (90%) of 5-bromo-8-nitroisoquinoline as a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-7db5e9af87b84bd0b93bea6e49f41bd0
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696229B2

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