3-hydroxy-6-methoxy-2-(4-methoxybenzyl)-3-(4-methoxyphenyl)-2,3-dihydro-isoindol-1-one

Base Information

• Chemical Name: 3-hydroxy-6-methoxy-2-(4-methoxybenzyl)-3-(4-methoxyphenyl)-2,3-dihydro-isoindol-1-one
• CAS No.: 320371-33-3
• Molecular Formula: C₂₄H₂₃NO₅
• Molecular Weight: 405.45

Synonyms:3-hydroxy-6-methoxy-2-(4-methoxybenzyl)-3-(4-methoxyphenyl)-2,3-dihydro-isoindol-1-one

Chemical Property of 3-hydroxy-6-methoxy-2-(4-methoxybenzyl)-3-(4-methoxyphenyl)-2,3-dihydro-isoindol-1-one

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Technology Process of 3-hydroxy-6-methoxy-2-(4-methoxybenzyl)-3-(4-methoxyphenyl)-2,3-dihydro-isoindol-1-one

There total 5 articles about 3-hydroxy-6-methoxy-2-(4-methoxybenzyl)-3-(4-methoxyphenyl)-2,3-dihydro-isoindol-1-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: 89.0%

5-methoxy-2-(4-methoxybenzoyl)-benzoic acid (108837-29-2) + 4-methoxy-benzylamine (2393-23-9) → 3-hydroxy-6-methoxy-2-(4-methoxybenzyl)-3-(4-methoxyphenyl)-2,3-dihydro-isoindol-1-one (320371-33-3)

Guidance literature:

With diphenyl phosphoryl azide; triethylamine; In N,N-dimethyl-formamide; at -20 ℃; for 6h;

DOI:10.1016/S0968-0896(00)00194-2

Reference yield: 22.0%

4-methoxy-benzylamine (2393-23-9) + 5-methoxy-2-(4-methoxy-benzoyl)-benzoyl chloride → 3-hydroxy-6-methoxy-2-(4-methoxybenzyl)-3-(4-methoxyphenyl)-2,3-dihydro-isoindol-1-one (320371-33-3) + 6-methoxy-2-(4-methoxybenzyl)-3-(4-methoxybenzylamino)-3-(4-methoxyphenyl)-2,3-dihydroisoindol-1-one

Guidance literature:

In dichloromethane;

DOI:10.1016/S0968-0896(00)00194-2

Reference yield:

methyl 4-methoxybenzoate (121-98-2) → 3-hydroxy-6-methoxy-2-(4-methoxybenzyl)-3-(4-methoxyphenyl)-2,3-dihydro-isoindol-1-one (320371-33-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 43 percent / n-BuLi / tetrahydrofuran; cyclohexane / 2 h / -95 °C

2: SOCl₂ / CH₂Cl₂ / 20 °C

3: 21 percent / CH₂Cl₂

With n-butyllithium; thionyl chloride; In tetrahydrofuran; dichloromethane; cyclohexane; 1: Condensation / 2: Chlorination / 3: Condensation;

DOI:10.1016/S0968-0896(00)00194-2

upstream raw materials:

5-methoxy-2-(4-methoxybenzoyl)-benzoic acid

4-methoxy-benzylamine

methyl 4-methoxybenzoate

2-bromo-5-methoxy-benzoic acid

Downstream raw materials:

7-methoxy-3,4-bis(4-methoxyphenyl)-2H-isoquinolin-1-one

7-methoxy-3,4-bis-(4-methoxy-phenyl)-isoquinoline

1-chloro-5-methoxy-3,4-bis(4-methoxyphenyl)-isoquinoline

N'-[7-methoxy-3,4-bis-(4-methoxy-phenyl)-isoquinolin-1-yl]-N,N-dimethyl-ethane-1,2-diamine

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