1-(2-bromo-5-hydroxy-4-methoxy-benzyl)-1,3,4,7,8,8a-hexahydro-2H-isoquinolin-6-one

Base Information

Chemical Name:1-(2-bromo-5-hydroxy-4-methoxy-benzyl)-1,3,4,7,8,8a-hexahydro-2H-isoquinolin-6-one
CAS No.:54186-35-5
Molecular Formula:C₁₇H₂₀BrNO₃
Molecular Weight:366.255
Hs Code.:

1-(2-bromo-5-hydroxy-4-methoxy-benzyl)-1,3,4,7,8,8a-hexahydro-2<i>H</i>-isoquinolin-6-one

Synonyms:1-(2-bromo-5-hydroxy-4-methoxy-benzyl)-1,3,4,7,8,8a-hexahydro-2H-isoquinolin-6-one

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Chemical Property of 1-(2-bromo-5-hydroxy-4-methoxy-benzyl)-1,3,4,7,8,8a-hexahydro-2H-isoquinolin-6-one

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Technology Process of 1-(2-bromo-5-hydroxy-4-methoxy-benzyl)-1,3,4,7,8,8a-hexahydro-2H-isoquinolin-6-one

There total 7 articles about 1-(2-bromo-5-hydroxy-4-methoxy-benzyl)-1,3,4,7,8,8a-hexahydro-2H-isoquinolin-6-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

: 74007-25-3
1-(2-Bromo-5-hydroxy-4-methoxy-benzyl)-1,3,4,5,7,8-hexahydro-2H-isoquinolin-6-one

: 54186-35-5
1-(2-bromo-5-hydroxy-4-methoxy-benzyl)-1,3,4,7,8,8a-hexahydro-2H-isoquinolin-6-one

Guidance literature:: With hydrogen bromide; at 25 ℃; for 48h;
DOI:10.1021/jo01303a045

Reference yield:

: 1131-94-8
homoisovanillic acid

: 54186-35-5
1-(2-bromo-5-hydroxy-4-methoxy-benzyl)-1,3,4,7,8,8a-hexahydro-2H-isoquinolin-6-one

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / 2 h / 200 °C

2: 2)Na(CN)BH₃ / 1) cyclization, neutralization to pH 4-5 with concentrated aqueous NH₃ 2) reduction with Na(CN)BH₃ in refluxing 65percent MeOH for 1.5h

3: 90 percent / Li, NH₃ (liquid) / tetrahydrofuran; 2-methyl-propan-2-ol / 1) 4h -55 to -65 deg C 2) 1.5h -75 deg C

With ammonia; lithium; sodium cyanoborohydride; In tetrahydrofuran; tert-butyl alcohol;
DOI:10.1021/jo01303a045

Reference yield:

: 23180-27-0
1-(3'-hydroxy-4'-methoxy-benzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline

: 54186-35-5
1-(2-bromo-5-hydroxy-4-methoxy-benzyl)-1,3,4,7,8,8a-hexahydro-2H-isoquinolin-6-one

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / Li, NH₃ (liquid) / tetrahydrofuran; 2-methyl-propan-2-ol / 1) 4h -55 to -65 deg C 2) 1.5h -75 deg C

With ammonia; lithium; In tetrahydrofuran; tert-butyl alcohol;
DOI:10.1021/jo01303a045