2-(4-chlorobenzyl)-3-(4-methoxyphenyl)-2-methyl-N-(quinolin-8-yl)propanamide

Base Information

Chemical Name:2-(4-chlorobenzyl)-3-(4-methoxyphenyl)-2-methyl-N-(quinolin-8-yl)propanamide
CAS No.:1429896-40-1
Molecular Formula:C₂₇H₂₅ClN₂O₂
Molecular Weight:444.961
Hs Code.:

Synonyms:2-(4-chlorobenzyl)-3-(4-methoxyphenyl)-2-methyl-N-(quinolin-8-yl)propanamide

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Chemical Property of 2-(4-chlorobenzyl)-3-(4-methoxyphenyl)-2-methyl-N-(quinolin-8-yl)propanamide

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Technology Process of 2-(4-chlorobenzyl)-3-(4-methoxyphenyl)-2-methyl-N-(quinolin-8-yl)propanamide

There total 5 articles about 2-(4-chlorobenzyl)-3-(4-methoxyphenyl)-2-methyl-N-(quinolin-8-yl)propanamide 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: 71.0%

: 1429896-54-7
3-(4-chlorophenyl)-2,2-dimethyl-N-(quinolin-8-yl)propanamide

: 13139-86-1
4-methoxyphenyl magnesium bromide

: 1429896-40-1
2-(4-chlorobenzyl)-3-(4-methoxyphenyl)-2-methyl-N-(quinolin-8-yl)propanamide

Guidance literature:: 3-(4-chlorophenyl)-2,2-dimethyl-N-(quinolin-8-yl)propanamide; 4-methoxyphenyl magnesium bromide; With N,N,N,N,-tetramethylethylenediamine; zinc dibromide; In tetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere;

With iron(III)-acetylacetonate; 1,2-dichloro-2-methylpropane; o-phenylenebis(diphenylphosphine); In tetrahydrofuran; at 20 - 50 ℃; for 36h;
DOI:10.1021/ja402806f

Reference yield:

: 622-95-7
4-chlorobenzyl bromide

: 1429896-40-1
2-(4-chlorobenzyl)-3-(4-methoxyphenyl)-2-methyl-N-(quinolin-8-yl)propanamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

1.2: 16 h / 20 °C / Inert atmosphere

2.1: sodium hydroxide / methanol / 60 °C

2.2: pH 2

3.1: thionyl chloride / 3 h / 85 °C / Inert atmosphere

4.1: triethylamine / dichloromethane / 0 - 20 °C

5.1: N,N,N,N,-tetramethylethylenediamine; zinc dibromide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

5.2: 36 h / 20 - 50 °C

With n-butyllithium; thionyl chloride; N,N,N,N,-tetramethylethylenediamine; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; zinc dibromide; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1021/ja402806f

Reference yield:

: 14305-27-2
3-(4-chlorophenyl)-2,2-dimethylpropanoic acid methyl ester

: 1429896-40-1
2-(4-chlorobenzyl)-3-(4-methoxyphenyl)-2-methyl-N-(quinolin-8-yl)propanamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydroxide / methanol / 60 °C

1.2: pH 2

2.1: thionyl chloride / 3 h / 85 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 0 - 20 °C

4.1: N,N,N,N,-tetramethylethylenediamine; zinc dibromide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

4.2: 36 h / 20 - 50 °C

With thionyl chloride; N,N,N,N,-tetramethylethylenediamine; triethylamine; sodium hydroxide; zinc dibromide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja402806f