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

Reaktionsgleichung

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

Edukt 2

HCID 260Hydrogen Bromide

HCID 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

customat room temperature
temperaturecool
customthe reaction to room temperature
concentrationconcentrate under reduced pressure
customTriturate with ethyl acetate
filtrationfilter

Quellen und Nachweise

ORD-Eintrag: ord-d2dbbf431f6444498cabd91ee04aa236
Quelldatensatz: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07381719B2

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