54396-25-7

Basic information

• Product Name: 2-oxo-N-phenyl-chromene-3-carboxamide
• Synonyms: 2-oxo-N-phenyl-chromene-3-carboxamide;2-oxo-N-phenyl-2H-chromene-3-carboxamide
• CAS NO: 54396-25-7
• Molecular Formula: C₁₆H₁₁NO₃
• Molecular Weight: 265.26344
• Mol File: 54396-25-7.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 539.8°Cat760mmHg
• Flash Point: 280.3°C
• Appearance: /
• Density: 1.369g/cm³
• Vapor Pressure: 1.01E-11mmHg at 25°C
• Refractive Index: 1.683
• CAS DataBase Reference: 2-oxo-N-phenyl-chromene-3-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-oxo-N-phenyl-chromene-3-carboxamide(54396-25-7)
• EPA Substance Registry System: 2-oxo-N-phenyl-chromene-3-carboxamide(54396-25-7)

Safety Data

• Hazardous Substances Data: 54396-25-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 22, p. 257, 1985 DOI: 10.1002/jhet.5570220203

InChI:InChI=1/C16H11NO3/c18-15(17-12-7-2-1-3-8-12)13-10-11-6-4-5-9-14(11)20-16(13)19/h1-10H,(H,17,18)

Upstream product

• 110-89-4 piperidine 
• 779-84-0 N-phenylsalicylaldimine 
• 105-53-3 diethyl malonate 
• 1846-76-0 ethyl coumarin-3-carboxylate 
• 62-53-3 aniline 
• 621-10-3 N,N'-diphenylmalonamide 
• 90-02-8 salicylaldehyde 
• 504-64-3 carbon suboxide 
• 886124-83-0 C₁₃H₈N₂O₃ 
• 1663-67-8 malonoyl dichloride 
• 531-81-7 2-oxo-2H-chromene-3-carboxylic acid 
• 3757-06-0 coumarin 3-carboxylic acid chloride 

Downstream Products

• 118428-98-1 C₁₆H₁₀ClNO₅S 
• 94-93-9 N,N'-ethylenebis(salicylideneimine) 
• 74556-15-3 N-(4-Bromo-phenyl)-2-[1-(2-nitro-phenyl)-meth-(E)-ylidene-hydrazinocarbonyl]-acetamide 
• 74556-14-2 N-(4-Bromo-phenyl)-2-[1-(2-hydroxy-phenyl)-meth-(E)-ylidene-hydrazinocarbonyl]-acetamide 
• 74556-16-4 N-(4-Bromo-phenyl)-2-[1-(4-methoxy-phenyl)-meth-(E)-ylidene-hydrazinocarbonyl]-acetamide 
• 74568-56-2 N-(4-Bromo-phenyl)-2-[(E)-3-phenyl-prop-2-en-(E)-ylidene-hydrazinocarbonyl]-acetamide 
• 74556-08-4 N-(4-Bromo-phenyl)-N'-furan-2-ylmethyl-malonamide 
• 74556-13-1 N-(4-Bromo-phenyl)-2-[1-phenyl-meth-(E)-ylidene-hydrazinocarbonyl]-acetamide 
• 74556-07-3 N-(4-Bromo-phenyl)-N'-butyl-malonamide 
• 74556-03-9 N-(4-Bromo-phenyl)-2-hydrazinocarbonyl-acetamide 
• 76152-10-8 N-furfurylsalicylaldimine 
• 2565-54-0 N-salicylidene-butylamine 
• 959-36-4 salicyaldehyde azine 
• 1015066-95-1 C₂₁H₂₀N₂O₇S 

Relevant articles and documents

The reaction between an azomethine and malonyl dichloride

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A Primary Amide-Functionalized Heterogeneous Catalyst for the Synthesis of Coumarin-3-carboxylic Acids via a Tandem Reaction

A crystalline primary amide-based bifunctional heterogeneous catalyst, {[Cd2(2-BPXG)(Fum)2(H2O)2]·2H2O}n (1) (where, 2-BPXG = 2,2′-((1,4-phenylenebis(methylene))bis((pyridin-2-ylmethyl)azanediyl)) diacetamide and Fum = fumarate), has been developed for the one-pot synthesis of a series of potentially biologically active coumarin-3-carboxylic acids at room temperature via a Knoevenagel-intramolecular cyclization tandem reaction. Catalyst 1 is prepared at room temperature from a one-pot self-assembly process in 81% yield and high purity within a few hours and has a ladder-like polymeric architecture based on single-crystal X-ray diffraction. Additional characterization of 1 includes elemental analysis, infrared spectroscopy, thermogravimetric analysis, and powder X-ray diffraction. Based on the optimized conditions, it is determined that 1 is highly efficient (conditions: 2 mol % catalyst, 3 h, and 26-28 °C in methanol) for this reaction. Its recyclability up to five cycles without significant loss of activity and structural integrity is also demonstrated. Using both electron-donating and electron-withdrawing substituents on the salicylaldehyde substrate, seven different derivatives of coumarin-3-carboxylic acid were made. Additionally, the monoamine oxidase (MAO) inhibitor, coumarin-3-phenylcarboxamide, has also been synthesized from coumarin-3-carboxylic acid obtained in the catalysis process. A detailed mechanism of action is also provided.

Synthesis of Multifunctionalized 2,3-Dihydro-4-pyridones and 4-Pyridones via the Reaction of Carbamoylated Enaminones with Aldehydes

The novel and effective diastereoselective synthesis of multifunctionalized dihydropyridones, including CF3-substituted derivatives, has been developed on the basis of the piperidine-promoted domino reaction of carbamoylated enaminones with ald