857629-78-8

Basic information

• Product Name: (E)-3-O-Methyl Entacapone
• Synonyms: (2E)-2-Cyano-N,N-diethyl-3-(4-hydroxy-3-Methoxy-5-nitrophenyl)-2-propenaMide;Entacapone 3-Methyl Ether;Entacapone IMpurity G;(E)-3-O-Methyl Entacapone;3-O-methylentacapone
• CAS NO: 857629-78-8
• Molecular Formula: C₁₅H₁₇N₃O₅
• Molecular Weight: 319.31258
• Product Categories: Amines;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 857629-78-8.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (E)-3-O-Methyl Entacapone(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3-O-Methyl Entacapone(857629-78-8)
• EPA Substance Registry System: (E)-3-O-Methyl Entacapone(857629-78-8)

Safety Data

• Hazardous Substances Data: 857629-78-8(Hazardous Substances Data)

Usage

Uses

Entacapone impurity (E558500).

Definition

ChEBI: A C-nitro compound that is entacapone in which the phenolic hydroxy group that is meta to the nitro group has been converted to the corresponding methyl ether.

Upstream product

• 893419-47-1 (2E)-2-cyano-3-(3-methoxy-4-hydroxy-phenyl)-N,N-diethylprop-2-enamide 
• 26391-06-0 2-cyano-N,N-diethylacetamide 
• 121-33-5 vanillin 
• 53793-77-4 2-cyano-N,N-diethylacrylamide 
• 203861-62-5 2-methoxy-4-iodophenol 
• 6635-20-7 isonitrovanillin 

Downstream Products

• 130929-57-6 entacapone 

Relevant articles and documents

Synthesis of entacapone by Pd-catalyzed heck coupling reaction

Synthesis of entacapone from 4-iodo-2-methoxy-phenol with 2-cyano-N,N-diethylacrylamide by palladium-catalyzed Heck reaction, as a key step, is described.

Efficient approach to pure entacapone and related compounds

A new and efficient process through a new intermediate, (2E)-2-cyano-3-(3,4-dihydroxy-5-nirtrophenyl)prop-2-enoic acid 15, has been described for preparing substantially pure entacapone 1. This new intermediate 15 was prepared by Knoevenagel condensation of 3,4-dihydroxy-5-nitrobenzaldehyde 2 with 2-cyanoacetic acid 14 and was further condensed with diethylamine to get pure entacapone 1. Some of the important process-related impurities of entacapone (17, 18, 19, and 20) were also prepared easily from this intermediate 15. Copyright Taylor & Francis Group, LLC.

A process for the preparation of entacapone

A process for the preparation of entacapone, in particular as the polymorphic form A, comprising the preparation of a compound of formula (V), as herein defined, by condensation of N,N-diethyl-cyano-acetamide with a compound of formula (IV), as herein defined, in the presence of a strong basic agent; the dealkylation of said compound of formula (V) to obtain entacapone and the crystallization thereof to the polymorphic form A.