1-[1-(4-Chlorophenyl)cyclobutyl]-7-methoxy-3,4-dihydroisoquinoline → 1-[1-(4-Chlorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-ol

HRID 1850866Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1850866
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22]C)[CH:20]=4)[CH2:15][CH2:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1>Br>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([OH:22])[CH:20]=4)[CH2:15][CH2:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Komponenten

3

Edukt 1

HCID 668686991-[1-(4-Chlorophenyl)cyclobutyl]-7-methoxy-3,4-dihydroisoquinoline

Produkt 1

HCID 582462431-[1-(4-Chlorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 260Hydrogen BromideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

The crude 1-[1-(4-chlorophenyl)cyclobutyl]-7-methoxy-3,4-dihydroisoquinoline (10.25 g, 30.8 mmol) was treated with 47% aqueous hydrobromic acid (109 mL) and stirred at 120° C. for 4 h. The reaction mixture was cooled to room temperature. The aqueous layer was decanted. The crude product was treated with dichloromethan, methanol and water and the pH was adjusted to 10 with aqueous 1N sodium hydroxide solution. The product precipitated and the solid was collected by filtration. The product was washed with water and dried in vacuo at 30° C. Yield: 3.56 g (30.3, 12.38 mmol).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe aqueous layer was decanted
  3. additionThe crude product was treated with dichloromethan, methanol and water
  4. customThe product precipitated
  5. filtrationthe solid was collected by filtration
  6. washThe product was washed with water
  7. customdried in vacuo at 30° C

Quellen und Nachweise

ORD-Eintrag
ord-704d909bc83b4dde9bd70089a44b837b
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957089B2

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