1-(6-(2-bromophenylamino)-5,8-dimethoxy-4,4-dimethyl-3,4-dihydroquinolin-1(2H)-yl)ethanone

Base Information

• Chemical Name: 1-(6-(2-bromophenylamino)-5,8-dimethoxy-4,4-dimethyl-3,4-dihydroquinolin-1(2H)-yl)ethanone
• CAS No.: 1315482-18-8
• Molecular Formula: C₂₁H₂₅BrN₂O₃
• Molecular Weight: 433.345
• Mol file: 1315482-18-8.mol

Synonyms:

Chemical Property of 1-(6-(2-bromophenylamino)-5,8-dimethoxy-4,4-dimethyl-3,4-dihydroquinolin-1(2H)-yl)ethanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(6-(2-bromophenylamino)-5,8-dimethoxy-4,4-dimethyl-3,4-dihydroquinolin-1(2H)-yl)ethanone

There total 6 articles about 1-(6-(2-bromophenylamino)-5,8-dimethoxy-4,4-dimethyl-3,4-dihydroquinolin-1(2H)-yl)ethanone 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: 74.0%

1-Bromo-2-iodobenzene (583-55-1) + 1-(6-amino-5,8-dimethoxy-4,4-dimethyl-3,4-dihydroquinolin-1(2H)-yl)ethanone (1315482-15-5) → 1-(6-(2-bromophenylamino)-5,8-dimethoxy-4,4-dimethyl-3,4-dihydroquinolin-1(2H)-yl)ethanone (1315482-18-8)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; for 18h; Inert atmosphere; Reflux; Sealed tube;

DOI:10.1055/s-0030-1260015

Reference yield:

2,5-dimethoxy-N-(3-methylbut-2-enyl)benzenamine (433714-29-5) → 1-(6-(2-bromophenylamino)-5,8-dimethoxy-4,4-dimethyl-3,4-dihydroquinolin-1(2H)-yl)ethanone (1315482-18-8)

Guidance literature:

Multi-step reaction with 5 steps

1: sulfuric acid / 0.42 h / 0 °C

2: pyridine / 18 h / 20 °C / Inert atmosphere

3: nitric acid / dichloromethane / 2 h / 0 °C / Inert atmosphere

4: palladium on carbon; hydrogen / tetrahydrofuran; ethanol / 18 h / 20 °C / 775.74 Torr

5: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / 1,4-dioxane / 18 h / Inert atmosphere; Reflux; Sealed tube

With pyridine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sulfuric acid; palladium on carbon; hydrogen; nitric acid; potassium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; 5: Hartwig-Buchwald coupling;

DOI:10.1055/s-0030-1260015

Reference yield:

5,8-dimethoxy-4,4-dimethyl-1,2,3,4-tetrahydroquinoline (433714-30-8) → 1-(6-(2-bromophenylamino)-5,8-dimethoxy-4,4-dimethyl-3,4-dihydroquinolin-1(2H)-yl)ethanone (1315482-18-8)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 18 h / 20 °C / Inert atmosphere

2: nitric acid / dichloromethane / 2 h / 0 °C / Inert atmosphere

3: palladium on carbon; hydrogen / tetrahydrofuran; ethanol / 18 h / 20 °C / 775.74 Torr

4: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / 1,4-dioxane / 18 h / Inert atmosphere; Reflux; Sealed tube

With pyridine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; palladium on carbon; hydrogen; nitric acid; potassium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; 4: Hartwig-Buchwald coupling;

DOI:10.1055/s-0030-1260015

upstream raw materials:

1-Bromo-2-iodobenzene

1-(6-amino-5,8-dimethoxy-4,4-dimethyl-3,4-dihydroquinolin-1(2H)-yl)ethanone

2,5-dimethoxy-N-(3-methylbut-2-enyl)benzenamine

5,8-dimethoxy-4,4-dimethyl-1,2,3,4-tetrahydroquinoline