2-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-N-ethyl-8-methoxy-N-(2-methoxyethyl)-3-methylquinolin-5-amine

Base Information

• Chemical Name: 2-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-N-ethyl-8-methoxy-N-(2-methoxyethyl)-3-methylquinolin-5-amine
• CAS No.: 1415354-05-0
• Molecular Formula: C₂₆H₃₄N₂O₅
• Molecular Weight: 454.566

Synonyms:2-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-N-ethyl-8-methoxy-N-(2-methoxyethyl)-3-methylquinolin-5-amine

Chemical Property of 2-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-N-ethyl-8-methoxy-N-(2-methoxyethyl)-3-methylquinolin-5-amine

Chemical Property:

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Technology Process of 2-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-N-ethyl-8-methoxy-N-(2-methoxyethyl)-3-methylquinolin-5-amine

There total 6 articles about 2-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-N-ethyl-8-methoxy-N-(2-methoxyethyl)-3-methylquinolin-5-amine 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: 56.1%

2-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-8-methoxy-N-(2-methoxyethyl)-3-methylquinolin-5-amine (1415354-04-9) + acetaldehyde (75-07-0,9002-91-9) → 2-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-N-ethyl-8-methoxy-N-(2-methoxyethyl)-3-methylquinolin-5-amine (1415354-05-0)

Guidance literature:

With sodium tris(acetoxy)borohydride; acetic acid; In tetrahydrofuran; at 20 ℃; for 15h;

DOI:10.1016/j.bmc.2012.09.028 DOI:10.1016/j.bmc.2012.09.028

Reference yield:

2-chloro-8-methoxy-3-methylquinoline (132118-31-1) → 2-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-N-ethyl-8-methoxy-N-(2-methoxyethyl)-3-methylquinolin-5-amine (1415354-05-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sulfuric acid; nitric acid / 3.5 h / -10 - 20 °C

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / water; 1,4-dioxane / 1.5 h / Reflux

3.1: ammonium chloride; iron / water; ethanol / 1 h / Reflux

4.1: triethylamine / dichloromethane / 16 h / 20 °C

5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 20 °C

5.2: 1 h / 40 °C

6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

7.1: sodium tris(acetoxy)borohydride; acetic acid / tetrahydrofuran / 15 h / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; nitric acid; sodium tris(acetoxy)borohydride; iron; sodium hydride; potassium carbonate; ammonium chloride; acetic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; 2.1: |Suzuki-Miyaura Coupling;

DOI:10.1016/j.bmc.2012.09.028 DOI:10.1016/j.bmc.2012.09.028

Reference yield:

2-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-8-methoxy-3-methyl-5-nitroquinoline (1415353-99-9) → 2-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-N-ethyl-8-methoxy-N-(2-methoxyethyl)-3-methylquinolin-5-amine (1415354-05-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: ammonium chloride; iron / water; ethanol / 1 h / Reflux

2.1: triethylamine / dichloromethane / 16 h / 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 20 °C

3.2: 1 h / 40 °C

4.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

5.1: sodium tris(acetoxy)borohydride; acetic acid / tetrahydrofuran / 15 h / 20 °C

With sodium tris(acetoxy)borohydride; iron; sodium hydride; ammonium chloride; acetic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.bmc.2012.09.028 DOI:10.1016/j.bmc.2012.09.028

upstream raw materials:

2-chloro-8-methoxy-3-methylquinoline

2-chloro-8-methoxy-3-methyl-5-nitroquinoline

2-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-8-methoxy-3-methyl-5-nitroquinoline

2-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-8-methoxy-3-methylquinolin-5-amine

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