4-[5-(diethylamino)-8-methoxy-3-methylquinolin-2-yl]-3,5-dimethoxybenzonitrile

Base Information

• Chemical Name: 4-[5-(diethylamino)-8-methoxy-3-methylquinolin-2-yl]-3,5-dimethoxybenzonitrile
• CAS No.: 1415354-14-1
• Molecular Formula: C₂₄H₂₇N₃O₃
• Molecular Weight: 405.497
• Mol file: 1415354-14-1.mol

Synonyms:4-[5-(diethylamino)-8-methoxy-3-methylquinolin-2-yl]-3,5-dimethoxybenzonitrile

Chemical Property of 4-[5-(diethylamino)-8-methoxy-3-methylquinolin-2-yl]-3,5-dimethoxybenzonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[5-(diethylamino)-8-methoxy-3-methylquinolin-2-yl]-3,5-dimethoxybenzonitrile

There total 3 articles about 4-[5-(diethylamino)-8-methoxy-3-methylquinolin-2-yl]-3,5-dimethoxybenzonitrile 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: 77.3%

4-(5-amino-8-methoxy-3-methylquinolin-2-yl)-3,5-dimethoxybenzonitrile (1415354-11-8) + acetaldehyde (75-07-0,9002-91-9) → 4-[5-(diethylamino)-8-methoxy-3-methylquinolin-2-yl]-3,5-dimethoxybenzonitrile (1415354-14-1)

Guidance literature:

With sodium tris(acetoxy)borohydride; acetic acid; In ethanol; at 20 ℃; for 4.5h;

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

Reference yield:

2-chloro-8-methoxy-3-methyl-5-nitroquinoline (1407104-66-8) → 4-[5-(diethylamino)-8-methoxy-3-methylquinolin-2-yl]-3,5-dimethoxybenzonitrile (1415354-14-1)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: sodium tris(acetoxy)borohydride; acetic acid / ethanol / 4.5 h / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium tris(acetoxy)borohydride; iron; potassium carbonate; ammonium chloride; acetic acid; In 1,4-dioxane; ethanol; water;

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

Reference yield:

N-(2-methoxyphenyl)propionamide (7157-34-8) → 4-[5-(diethylamino)-8-methoxy-3-methylquinolin-2-yl]-3,5-dimethoxybenzonitrile (1415354-14-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: trichlorophosphate / 0.25 h / 0 °C

1.2: 2.5 h / 70 °C

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

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

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

5.1: sodium tris(acetoxy)borohydride; acetic acid / ethanol / 4.5 h / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; nitric acid; sodium tris(acetoxy)borohydride; iron; potassium carbonate; ammonium chloride; acetic acid; trichlorophosphate; In 1,4-dioxane; ethanol; water;

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

upstream raw materials:

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

4-(5-amino-8-methoxy-3-methylquinolin-2-yl)-3,5-dimethoxybenzonitrile

acetaldehyde

N-(2-methoxyphenyl)propionamide

Refernces

• 1、 Takeda, Kunitoshi,Terauchi, Taro,Hashizume, Minako,Shikata, Kohdoh,Taguchi, Ryota,Murata-Tai, Kaoru,Fujisawa, Masae,Takahashi, Yoshinori,Shin, Kogyoku,Ino, Mitsuhiro,Shibata, Hisashi,Yonaga, Masahiro. "Synthesis and structure-activity relationships of 8-substituted-2-aryl-5- alkylaminoquinolines: Potent, orally active corticotropin-releasing factor-1 receptor antagonists". . p. 6559 - 6578. Retrieved 2013/01/15.