893419-47-1

Basic information

• Product Name: 2-cyano-N,N-diethyl-3-(4-hydroxy-3-methoxyphenyl)acrylamide
• Synonyms: 2-cyano-N,N-diethyl-3-(4-hydroxy-3-methoxyphenyl)acrylamide
• CAS NO: 893419-47-1
• Molecular Formula: C₁₅H₁₈N₂O₃
• Molecular Weight: 274.31502
• Mol File: 893419-47-1.mol

Chemical Properties

• Boiling Point: 481.4±45.0 °C(Predicted)
• Appearance: /
• Density: 1.177±0.06 g/cm3(Predicted)
• PKA: 9.35±0.31(Predicted)
• CAS DataBase Reference: 2-cyano-N,N-diethyl-3-(4-hydroxy-3-methoxyphenyl)acrylamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-cyano-N,N-diethyl-3-(4-hydroxy-3-methoxyphenyl)acrylamide(893419-47-1)
• EPA Substance Registry System: 2-cyano-N,N-diethyl-3-(4-hydroxy-3-methoxyphenyl)acrylamide(893419-47-1)

Safety Data

• Hazardous Substances Data: 893419-47-1(Hazardous Substances Data)

Upstream product

• 53793-77-4 2-cyano-N,N-diethylacrylamide 
• 203861-62-5 2-methoxy-4-iodophenol 
• 26391-06-0 2-cyano-N,N-diethylacetamide 
• 121-33-5 vanillin 

Downstream Products

• 857629-78-8 (2E)-2-cyano-3-(3-methoxy-4-hydroxy-5-nitro-phenyl)-N,Ndiethylprop-2-enamide 
• 130929-57-6 entacapone 
• 158693-04-0 (Z)-N,N-diethyl-2-cyano-3-(3-methoxy-4-hydroxy-5-nitro-phenyl)-acrylamide 

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.

PROCESS FOR THE PREPARATION OF ENTACAPONE AND ITS INTERMEDIATE THEREOF

Provided herein are processes for preparing a compound of Formula (V), comprising nitrating a compound of Formula (IV), with a nitrating agent in the presence of a catalyst.

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.

PROCESS FOR THE PREPARATION OF (E)-N,N-DIETHYL-2-CYANO-3(3,4-DIHYDROXY-5-NITRO-PHENYL)-ACRYLAMIDE IN STABLE POLYMORPHIC FORM AND INTERMEDIATES OF THE PROCESS

The invention relates to a process for the preparation of pure E isomer of N1N- diethyl-2-cyano-3-(3,4-dihydrìxy-t5-nitro-phenyl)-acryIamide of formula (1 ) ( D in stable polymorphic form. According to the invention _ (a) (E)-N, N-diethyl-2-cyano-3-(3-methoxy-4-hydroxy-5-nitro-phenyl)-acryl- amide is demethylated; or (b) (E)-N, N-diethyl-2-cyano-3-(3-methoxy-4-hydroxy-phenyl)-acrylamide is nitrated, and the. resulting (E)-N-, N-diethyl-2-cyano-3-(3-methoxy-4-hydroxy-5-nitro- phenyl)-acrylamide is demethylated; or - (c) vanillin is reacted with N.N-diethyl-cy.anoacetamide in the presence of a weak organic acid and of an amine compound used as catalysts, the resulting (E)- N,N-diethyl-2-cyano-3-(3-methoxy-4-hydroxy-phenyl)-acrylamide is nitrated, and the resulting (E)-N, N-diethyl-2-cyano-3-(3-methoxy-4-hydroxy-5-nitro-phenyl)-acrylamide is demethylated. The invention also relates to (E)-N, N-diethyl-2-cyano-3-(3-methoxy-4-hydroxy- phenyl)-acrylamide and (E)-N, N-diethyl-2-cyano-3-(3-rhethoxy-4-hydroxy-5-nitro- phenyl)-acrylamide and to their preparation.