7-Bromo-1-Chloroisoquinoline → 7-Bromo-1-butylisoquinoline

HRID 349055

Reaktionsgleichung

Reaktionsgleichung von HRID 349055
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2Cl)=[CH:4][CH:3]=1.[CH2:13]([Mg]Cl)[CH2:14][CH2:15][CH3:16]>C(OCC)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[CH2:13][CH2:14][CH2:15][CH3:16])=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 65020247-Bromo-1-ChloroisoquinolineHCID 178418265HCID 178418265, Verbindung

Produkt 1

HCID 210859957-Bromo-1-butylisoquinolineAusbeute 24,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a refluxing solution of 7-bromo-1-chloroisoquinoline (4.85 g, 23.28 mmol) in diethyl ether (75 mL) was added butylmagnesium chloride (17.8 mL, 2.0 M ether, 35.6 mmol) and the reaction maintained at reflux for 2 h. The reaction mixture was cooled to room temperature, carefully diluted with an equal volume of ethyl acetate, washed with saturated sodium bicarbonate, water, and saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure to give an brown oil. Purification by flash column chromatography (silica, 1–10% ether/hexanes) gave the desired 7-bromo-1-butylisoquinoline (1.50 g): ESI MS m/z 264 [M+H]+.

Aufarbeitung

  1. temperaturethe reaction maintained
  2. temperatureat reflux for 2 h
  3. washwashed with saturated sodium bicarbonate, water, and saturated sodium chloride
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give an brown oil
  8. customPurification by flash column chromatography (silica, 1–10% ether/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-08c206c12c7d441bac3b2682a3e116dc
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176242B2

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