Benzamide, 2-[hydroxy(4-methoxyphenyl)methyl]-N-methyl-

Base Information

• Chemical Name: Benzamide, 2-[hydroxy(4-methoxyphenyl)methyl]-N-methyl-
• CAS No.: 65492-57-1
• Molecular Formula: C16H17NO3
• Molecular Weight: 271.316
• Mol file: 65492-57-1.mol

Synonyms:

Chemical Property of Benzamide, 2-[hydroxy(4-methoxyphenyl)methyl]-N-methyl-

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzamide, 2-[hydroxy(4-methoxyphenyl)methyl]-N-methyl-

There total 4 articles about Benzamide, 2-[hydroxy(4-methoxyphenyl)methyl]-N-methyl- 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: 51.0%

N-methylbenzamide (88070-48-8) + 4-methoxy-benzaldehyde (123-11-5) → 3-(4-methoxyphenyl)phthalide (21615-74-7) + 2-[Hydroxy-(4-methoxy-phenyl)-methyl]-N-methyl-benzamide (65492-57-1) + 2-Methyl-3-(4-methoxyphenyl)-isoindolin-1-on

Guidance literature:

N-methylbenzamide; 4-methoxy-benzaldehyde; With rhenium(I) pentacarbonyl bromide; dimethyl zinc(II); zinc dibromide; In 1,2-dimethoxyethane; toluene; at 130 ℃; for 24h; Inert atmosphere; Schlenk technique;

With water; In 1,2-dimethoxyethane; toluene; at 20 ℃; chemoselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.9b02142

Reference yield:

benzoic acid (65-85-0,8013-63-6) → 3-(4-methoxyphenyl)phthalide (21615-74-7) + 2-[Hydroxy-(4-methoxy-phenyl)-methyl]-N-methyl-benzamide (65492-57-1) + 2-Methyl-3-(4-methoxyphenyl)-isoindolin-1-on

Guidance literature:

Multi-step reaction with 3 steps

1.1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 60 °C / Inert atmosphere; Schlenk technique

2.1: triethylamine / diethyl ether; methanol / 1 h / 20 °C / Inert atmosphere; Schlenk technique

3.1: rhenium(I) pentacarbonyl bromide; dimethyl zinc(II); zinc dibromide / 1,2-dimethoxyethane; toluene / 24 h / 130 °C / Inert atmosphere; Schlenk technique

3.2: 20 °C / Inert atmosphere; Schlenk technique

With thionyl chloride; rhenium(I) pentacarbonyl bromide; dimethyl zinc(II); triethylamine; N,N-dimethyl-formamide; zinc dibromide; In methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; toluene;

DOI:10.1021/acs.orglett.9b02142

Reference yield:

benzoyl chloride (98-88-4) → 3-(4-methoxyphenyl)phthalide (21615-74-7) + 2-[Hydroxy-(4-methoxy-phenyl)-methyl]-N-methyl-benzamide (65492-57-1) + 2-Methyl-3-(4-methoxyphenyl)-isoindolin-1-on

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / diethyl ether; methanol / 1 h / 20 °C / Inert atmosphere; Schlenk technique

2.1: rhenium(I) pentacarbonyl bromide; dimethyl zinc(II); zinc dibromide / 1,2-dimethoxyethane; toluene / 24 h / 130 °C / Inert atmosphere; Schlenk technique

2.2: 20 °C / Inert atmosphere; Schlenk technique

With rhenium(I) pentacarbonyl bromide; dimethyl zinc(II); triethylamine; zinc dibromide; In methanol; 1,2-dimethoxyethane; diethyl ether; toluene;

DOI:10.1021/acs.orglett.9b02142

upstream raw materials:

N-methylbenzamide

4-methoxy-benzaldehyde

benzoic acid

benzoyl chloride