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

반응식

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

참가 물질

반응물 2

HCID 260Hydrogen Bromide

HCID 393566-Methoxy-1,2,3,4-tetrahydroisoquinoline

생성물 1

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

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록: ord-d2dbbf431f6444498cabd91ee04aa236
출처 데이터셋: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07381719B2

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