1,4-Dibromobutane → 7-(4-Bromobutoxy)-3,4-dihydro-1(2h)-isoquinolinone

HRID 1750088Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1750088
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[Br:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.C([O-])([O-])=O.[K+].[K+]>CCO.O>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 442032017-Hydroxy-3,4-dihydro-2H-isoquinolin-1-one

Produkt 1

HCID 686269787-(4-Bromobutoxy)-3,4-dihydro-1(2h)-isoquinolinoneAusbeute 64,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of intermediate 19 (196 mg, 1.2 mmol), 1,4-dibromobutane (0.43 mL, 3.6 mmol) and anhydrous K2CO3 (166 mg, 1.22 mmol) was dissolved in EtOH (4 mL) and the solution was heated to reflux and stirred overnight. The mixture was diluted with water and extracted with EtOAc. The combined EtOAc layers were washed with water, brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by flash chromatography on silica gel column (elution with PE/EtOAc=3:1) to give 7-(4-bromobutoxy)-3,4-dihydroisoquinolin-1(2H)-one (intermediate 21) (230 mg, 63%) as a white solid.

Aufarbeitung

  1. temperaturethe solution was heated
  2. temperatureto reflux
  3. extractionextracted with EtOAc
  4. washThe combined EtOAc layers were washed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography on silica gel column (elution with PE/EtOAc=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-665f2fe296d7444ea6ad63db60b97c7a
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156822B2

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