(E/Z)-3-O-Methyl Entacapone

Base Information

• Chemical Name: (E/Z)-3-O-Methyl Entacapone
• CAS No.: 146698-91-1
• Molecular Formula: C15H17N3O5
• Molecular Weight: 319.317
• Mol file: 146698-91-1.mol

Synonyms:(E/Z)-3-O-Methyl Entacapone;(E/Z)-Entacapone 3-Methyl Ether;2-Cyano-N,N-diethyl-3-(4-hydroxy-3-Methoxy-5-nitrophenyl)-2-propenaMide

Chemical Property of (E/Z)-3-O-Methyl Entacapone

Chemical Property:

• Boiling Point: 514.1±50.0 °C(Predicted)
• PKA: 5.67±0.50(Predicted)
• PSA: 119.38000
• Density: 1.304±0.06 g/cm3(Predicted)
• LogP: 2.60758
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

(E/Z)-3-O-MethylEntacapone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Intermediate in the preparation of Entacapone (E558500).

Technology Process of (E/Z)-3-O-Methyl Entacapone

There total 3 articles about (E/Z)-3-O-Methyl Entacapone 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: 94.2%

isonitrovanillin (6635-20-7) + 2-cyano-N,N-diethylacetamide (26391-06-0) → 2-cyano-N,N-diethyl-3-(4-hydroxy-3-methoxy-5-nitrophenyl)prop-2-enamide (146698-91-1)

Guidance literature:

acetic acid; glycine; In toluene; for 12 - 15h; Heating / reflux;

Reference yield: 56.0%

2-cyano-3-(3,4-dimethoxy-5-nitrophenyl)-N,N-diethylprop-2-enamide → 2-cyano-N,N-diethyl-3-(4-hydroxy-3-methoxy-5-nitrophenyl)prop-2-enamide (146698-91-1)

Guidance literature:

2-cyano-3-(3,4-dimethoxy-5-nitrophenyl)-N,N-diethylprop-2-enamide; With triethylamine; In ethanol; at 70 - 75 ℃; for 12h;

With hydrogen iodide; In water;

DOI:10.1007/s12039-015-0961-4

Reference yield:

→ 2-cyano-N,N-diethyl-3-(4-hydroxy-3-methoxy-5-nitrophenyl)prop-2-enamide (146698-91-1)

Guidance literature:

With IRA 96 resin; In toluene; Reflux;

upstream raw materials:

isonitrovanillin

2-cyano-N,N-diethylacetamide

Downstream raw materials:

entacapone

(2Z)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide

Refernces

• 1、 Harisha, Attimogae Shivamurthy,Nayak, Suresh Parameshwar,Nagarajan, Kuppuswamy,Guru Row, Tayur Narasingarow,Hosamani, Amar A.. "Novel triethylamine mediated thermal reactions of 3-aryl-2-cyanoprop-2-enoic acid derivatives - Demethylation, reduction and vinylogation". supporting information. p. 1427 - 1431. Retrieved 2015/03/04.
• 2、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF ENTACAPONE". Page/Page column 14-15. . Retrieved 2008/06/13.