6-hydroxy-3,4-bis(4-hydroxy-3-methoxyphenyl)-7-methoxy-2H-pyrido[3,4-b]indol-1(9H)-one

Base Information

Chemical Name:6-hydroxy-3,4-bis(4-hydroxy-3-methoxyphenyl)-7-methoxy-2H-pyrido[3,4-b]indol-1(9H)-one
CAS No.:1333109-64-0
Molecular Formula:C₂₆H₂₂N₂O₇
Molecular Weight:474.47
Hs Code.:

Synonyms:6-hydroxy-3,4-bis(4-hydroxy-3-methoxyphenyl)-7-methoxy-2H-pyrido[3,4-b]indol-1(9H)-one

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Chemical Property of 6-hydroxy-3,4-bis(4-hydroxy-3-methoxyphenyl)-7-methoxy-2H-pyrido[3,4-b]indol-1(9H)-one

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Technology Process of 6-hydroxy-3,4-bis(4-hydroxy-3-methoxyphenyl)-7-methoxy-2H-pyrido[3,4-b]indol-1(9H)-one

There total 15 articles about 6-hydroxy-3,4-bis(4-hydroxy-3-methoxyphenyl)-7-methoxy-2H-pyrido[3,4-b]indol-1(9H)-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: 48.0%

: 1333109-61-7
9-benzyl-6-(benzyloxy)-3,4-bis(4-isopropoxy-3-methoxyphenyl)-7-methoxy-2H-pyrido[3,4-b]indol-1(9H)-one

: 1333109-64-0
6-hydroxy-3,4-bis(4-hydroxy-3-methoxyphenyl)-7-methoxy-2H-pyrido[3,4-b]indol-1(9H)-one

Guidance literature:: 9-benzyl-6-(benzyloxy)-3,4-bis(4-isopropoxy-3-methoxyphenyl)-7-methoxy-2H-pyrido[3,4-b]indol-1(9H)-one; With aluminum (III) chloride; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

With ammonium chloride; In dichloromethane; water; at 20 ℃; regioselective reaction;
DOI:10.1016/j.bmc.2011.06.056

Reference yield:

: 4-isopropoxy-3-methoxybenzoic acid isopropyl ester

: 1333109-64-0
6-hydroxy-3,4-bis(4-hydroxy-3-methoxyphenyl)-7-methoxy-2H-pyrido[3,4-b]indol-1(9H)-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: potassium hydroxide / ethanol; water / 4 h / Reflux

1.2: pH 3

2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

3.1: dmap / acetonitrile / 16 h / 20 °C / Inert atmosphere

4.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium diisopropyl amide / tetrahydrofuran; hexane / 8 h / -78 °C / Inert atmosphere

5.1: dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

6.1: triethylamine / tetrahydrofuran / 14 h / 20 °C / Inert atmosphere

7.1: trifluoroacetic acid / acetonitrile / 0.25 h / Reflux

8.1: aluminum (III) chloride / dichloromethane / 24 h / 20 °C / Inert atmosphere

8.2: 20 °C

With dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; aluminum (III) chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; potassium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; acetonitrile; 7.1: Friedel-Crafts cyclization;
DOI:10.1016/j.bmc.2011.06.056

Reference yield:

: 1333109-36-6
N-(4-isopropoxy-3-methoxybenzyl)-4-isopropoxy-3-methoxybenzamide

: 1333109-64-0
6-hydroxy-3,4-bis(4-hydroxy-3-methoxyphenyl)-7-methoxy-2H-pyrido[3,4-b]indol-1(9H)-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: dmap / acetonitrile / 16 h / 20 °C / Inert atmosphere

2.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium diisopropyl amide / tetrahydrofuran; hexane / 8 h / -78 °C / Inert atmosphere

3.1: dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

4.1: triethylamine / tetrahydrofuran / 14 h / 20 °C / Inert atmosphere

5.1: trifluoroacetic acid / acetonitrile / 0.25 h / Reflux

6.1: aluminum (III) chloride / dichloromethane / 24 h / 20 °C / Inert atmosphere

6.2: 20 °C

With dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; aluminum (III) chloride; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; acetonitrile; 5.1: Friedel-Crafts cyclization;
DOI:10.1016/j.bmc.2011.06.056