CIS-ENTACAPONE

Base Information

• Chemical Name: CIS-ENTACAPONE
• CAS No.: 145195-63-7
• Molecular Formula: C14H15 N3 O5
• Molecular Weight: 305.29
• Hs Code.: 2926900005
• Mol file: 145195-63-7.mol

Synonyms:2-Propenamide,2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-, (Z)-; (Z)-2-Cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide;(Z)-Entacapone

Chemical Property of CIS-ENTACAPONE

Chemical Property:

• Melting Point: 142-144°C
• PSA: 130.38000
• LogP: 2.30458
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Dichloromethane (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

cis-Entacapone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: cis-Entacapone is a metabolite of the catechol-O-methyltransferase (COMT) inhibitor entacapone . It is also a potential impurity found in commercial preparations of entacapone and a degradant of entacapone formed by UV light exposure.
• Uses: cis-Entacapone (Entacapone EP Impurity A) is the (Z)-Isomer of Entacapone polymorphic form B. Antiparkinsonian. (Z)-Isomer of Entacapone polymorphic form B. Antiparkinsonian

Technology Process of CIS-ENTACAPONE

There total 5 articles about CIS-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: 75.5%

2-cyano-N,N-diethylacetamide (26391-06-0) + 3,4-dihydroxy-5-nitrobenzaldehyde (116313-85-0) → entacapone (130929-57-6) + (2Z)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide (145195-63-7)

Guidance literature:

2-cyano-N,N-diethylacetamide; 3,4-dihydroxy-5-nitrobenzaldehyde; With piperidine; In isopropyl alcohol; for 12 - 15h; Heating / reflux;

With acetic acid; In isopropyl alcohol; at 20 ℃;

Reference yield:

2-cyano-N,N-diethyl-3-(4-hydroxy-3-methoxy-5-nitrophenyl)prop-2-enamide (146698-91-1) → entacapone (130929-57-6) + (2Z)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide (145195-63-7)

Guidance literature:

With pyridine; aluminum (III) chloride; In dichloromethane; at 0 - 55 ℃; for 3.08333 - 4.25h;

Reference yield:

2-cyano-N,N-diethylacetamide (26391-06-0) + 3,4-dihydroxy-5-nitrobenzaldehyde (116313-85-0) → (2Z)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide (145195-63-7)

Guidance literature:

2-cyano-N,N-diethylacetamide; 3,4-dihydroxy-5-nitrobenzaldehyde; In toluene; at 108 - 112 ℃; Dean-Stark;

With acetic acid; In toluene; at 5 ℃; for 4h; Reflux;

upstream raw materials:

2-cyano-N,N-diethylacetamide

3,4-dihydroxy-5-nitrobenzaldehyde

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

entacapone

Downstream raw materials:

entacapone; sodium salt

entacapone; piperidine salt

entacapone

Refernces

• 1、 -. "AN IMPROVED PROCESS FOR PREPARATION OF (2E)-2-CYANO-3-(3,4- DIHYDROXY-5-NITROPHENYL)N,N-DIETHYL-2-PROPENAMIDE POLYMORPHIC FORM A". Page/Page column 7-8. . Retrieved 2009/08/14.
• 2、 -. "PROCESS FOR MANUFACTURING ENTACAPONE". Page/Page column 9-11. . Retrieved 2008/06/13.