1-(2'-bromo-4'-methoxy-5'-hydroxybenzyl)-2-formyl-1,3,4,5,7,8-hexahydroisoquinolin-6-one

Base Information

Chemical Name:1-(2'-bromo-4'-methoxy-5'-hydroxybenzyl)-2-formyl-1,3,4,5,7,8-hexahydroisoquinolin-6-one
CAS No.:74007-24-2
Molecular Formula:C₁₈H₂₀BrNO₄
Molecular Weight:394.265
Hs Code.:

Synonyms:1-(2'-bromo-4'-methoxy-5'-hydroxybenzyl)-2-formyl-1,3,4,5,7,8-hexahydroisoquinolin-6-one

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Chemical Property of 1-(2'-bromo-4'-methoxy-5'-hydroxybenzyl)-2-formyl-1,3,4,5,7,8-hexahydroisoquinolin-6-one

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Technology Process of 1-(2'-bromo-4'-methoxy-5'-hydroxybenzyl)-2-formyl-1,3,4,5,7,8-hexahydroisoquinolin-6-one

There total 13 articles about 1-(2'-bromo-4'-methoxy-5'-hydroxybenzyl)-2-formyl-1,3,4,5,7,8-hexahydroisoquinolin-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: 65.0%

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

: 1864-94-4
phenyl formate

: 74007-24-2
1-(2'-bromo-4'-methoxy-5'-hydroxybenzyl)-2-formyl-1,3,4,5,7,8-hexahydroisoquinolin-6-one

Guidance literature:: In chloroform; Heating;
DOI:10.1021/jo01303a045

Reference yield:

: 74007-23-1
1-(2'-bromo-4'-methoxy-5'-hydroxybenzyl)-2-formyl-6-ketal-1,3,4,5,7,8-hexahydroisoquinoline

: 74007-24-2
1-(2'-bromo-4'-methoxy-5'-hydroxybenzyl)-2-formyl-1,3,4,5,7,8-hexahydroisoquinolin-6-one

Guidance literature:: With formic acid; at 25 ℃; for 1h; Yield given;
DOI:10.1021/jo01303a045

Reference yield:

: 1131-94-8
homoisovanillic acid

: 74007-24-2
1-(2'-bromo-4'-methoxy-5'-hydroxybenzyl)-2-formyl-1,3,4,5,7,8-hexahydroisoquinolin-6-one

Guidance literature:: Multi-step reaction with 6 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

5: 87 percent / CHCl₃ / Heating

6: NaOMe / methanol

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