Hydrogen Bromide → 1,2,3,4-Tetrahydroisoquinolin-6-ol

HRID 131020

Reaktionsgleichung

Reaktionsgleichung von HRID 131020
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:7][CH2:6]2.Br>>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:7][CH2:6]2

Komponenten

3

Edukt 2

HCID 260Hydrogen BromideHCID 393566-Methoxy-1,2,3,4-tetrahydroisoquinoline

Produkt 1

HCID 266981,2,3,4-Tetrahydroisoquinolin-6-olAusbeute 100 %

Versuchsvorschrift

Combine 6-Methoxy-1,2,3,4-tetrahydro-isoquinoline (5.0, 20.5 mmol) and 48% HBr(aq), 20 ml at room temperature. After the reaction refluxes for 24 hours, cool the reaction to room temperature and concentrate under reduced pressure. Triturate with ethyl acetate and filter to afford 5.5 g, 20.5 mmol (99% yield) of the title compound as a tan solid: 1H NMR (500 MHz, DMSO); 2.8-2.9 (2H, m), 3.3-3.4 (2H, m), 4.1 (2H, s), 6.5-6.7 (2H, m), 6.9-7.1 (1H, m), 8.8-9.0 (2H, br s), 9.4-9.5 (1H, s).

Aufarbeitung

  1. customat room temperature
  2. temperaturecool
  3. customthe reaction to room temperature
  4. concentrationconcentrate under reduced pressure
  5. customTriturate with ethyl acetate
  6. filtrationfilter

Quellen und Nachweise

ORD-Eintrag
ord-d2dbbf431f6444498cabd91ee04aa236
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381719B2

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