Ammonia → 4-Aminoisoquinoline

HRID 10547

Reaktionsgleichung

Reaktionsgleichung von HRID 10547
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4][CH:3]=1.[NH3:12]>O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].O1CCOCC1>[NH2:12][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 222AmmoniaHCID 737434-Bromoisoquinoline

Produkt 1

HCID 902374-Aminoisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24463Copper sulfate pentahydrateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
165 °C

Versuchsvorschrift

A suspension of 4-bromoisoquinoline (25.0 g), copper(II) sulfate pentahydrate (30.4 g, Nacalai Tesque), 28% aqueous ammonia (100 ml) and 1,4-dioxane (100 ml) was stirred in a sealed tube at 165° C. for 21 hours. The reaction mixture was cooled to room temperature, the insoluble matters were removed by filtration through Celite, and the filtrate was extracted twice with ethyl acetate (150 ml for each time). The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=9:1) to obtain the title compound (13.2 g).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe insoluble matters were removed by filtration through Celite
  3. extractionthe filtrate was extracted twice with ethyl acetate (150 ml for each time)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform:methanol=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-5ea2cb1dd9a846b5bf3301835d03cccb
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094789B2

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