Phosphorus oxychloride → 1-chloro-7-nitroisoquinoline

HRID 1070464Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1070464
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][N+:10]([O-])=[CH:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].P(Cl)(Cl)([Cl:17])=O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Cl:17][C:11]1[C:12]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=2)[CH:8]=[CH:9][N:10]=1

Komponenten

5

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 21862656HCID 21862656, Verbindung

Produkt 1

HCID 218626571-chloro-7-nitroisoquinolineAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a suspension of 7-nitroisoquinoline N-oxide obtained in Preparation Example 1-5, Step 3 in toluene (185 ml) was added phosphorus oxychloride (3.5 ml, 37 mmol), and the mixture was stirred under heating at 90° C. for 2 hr. The reaction mixture was cooled to room temperature and the reaction mixture was poured into an aqueous sodium hydrogencarbonate solution. The aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:acetone=30:1) to give 1-chloro-7-nitroisoquinoline (540 mg, 14%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform:acetone=30:1)

Quellen und Nachweise

ORD-Eintrag
ord-848fa20054324ab49142b0e3bd91b254
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903094B2

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