Sodium Carbonate → 5-Bromo-8-nitroisoquinoline

HRID 272774

Reaktionsgleichung

Reaktionsgleichung von HRID 272774
[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+].C([O-])([O-])=O.[Na+].[Na+]>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

5

Edukt 3

HCID 10340Sodium CarbonateHCID 24434Potassium NitrateHCID 7364875-Bromoisoquinoline

Produkt 1

HCID 8169835-Bromo-8-nitroisoquinolineAusbeute 99,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel2×

Versuchsvorschrift

5-Bromo-isoquinoline (100 mg, 0.48 mmol) was suspended in 0.58 mL of concentrated H2SO4. To this solution was added KNO3 (68 mg, 0.58 mmol) in 0.48 mL of concentrated H2SO4. The reaction mixture was stirred at room temperature for 1.5 hours, poured into water/ice, neutralized with 2.0 M Na2CO3, and extracted with EtOAc three times The combined organic layers were washed brine, dried (MgSO4), filtered and concentrated under vacuum to give 121 mg of the title product. MS (DCI) m/e 255 (M+H)+; 1H NMR (500 MHz, CDCl3) δ 10.0 (s, 1H), 9.39 (s, 1H), 8.85 (d, J=5.76 Hz, 1H), 8.17-8.22 (m, 2H), 8.12 (d, J=8.14 Hz, 1H).

Aufarbeitung

  1. extractionextracted with EtOAc three times The combined organic layers
  2. washwere washed brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b18b032ac6db43558af4c781acd38ea5
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456169B2

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