1374118-80-5

Basic information

• Product Name: methyl 4-(4-methylphenylamino)-1-(4-methylphenyl)-2, 5-dihydro-5-oxo-1H-pyrrole-3-carboxylate
• Synonyms: methyl 4-(4-methylphenylamino)-1-(4-methylphenyl)-2, 5-dihydro-5-oxo-1H-pyrrole-3-carboxylate
• CAS NO: 1374118-80-5
• Molecular Weight: 336.39
• Mol File: 1374118-80-5.mol

Chemical Properties

• CAS DataBase Reference: methyl 4-(4-methylphenylamino)-1-(4-methylphenyl)-2, 5-dihydro-5-oxo-1H-pyrrole-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-(4-methylphenylamino)-1-(4-methylphenyl)-2, 5-dihydro-5-oxo-1H-pyrrole-3-carboxylate(1374118-80-5)
• EPA Substance Registry System: methyl 4-(4-methylphenylamino)-1-(4-methylphenyl)-2, 5-dihydro-5-oxo-1H-pyrrole-3-carboxylate(1374118-80-5)

Safety Data

• Hazardous Substances Data: 1374118-80-5(Hazardous Substances Data)

Upstream product

• 50-00-0 formaldehyd 
• 106-49-0 p-toluidine 
• 87748-33-2 methyl 3-carbomethoxy-3-(4'-methylphenyl)amino-2-propenoate 
• 762-42-5 dimethyl acetylenedicarboxylate 

Relevant articles and documents

Imin-based synthesis of polyfunctionalized dihydro-2-oxypyrroles catalyzed by glycine amino acid via tandem Michael–Mannich cyclocondensation reaction under ambient temperature

An efficient and mild synthetic route to the convenient one-pot preparation of polyfunctionalized dihydro-2-oxypyrroles has been developed and catalyzed via glycine amino acid as a natural bio-based and biodegradable catalyst using imin-based four condensation domino reaction of amines, dialkyl acetylenedicarboxylates and formaldehyde via tandem Michael–Mannich cyclocondensation reaction under ambient temperature. The reactions complete in less time, but the products are obtained in outstanding yields. This environmentally friendly method includes the noticeable properties such as bio-based and green catalyst, direct workup without column chromatographic separation, cost-effective, mild and simple synthesis, one-pot procedure and high atom economy.

Multi-component synthesis of piperidines and dihydropyrrol-2-one derivatives catalyzed by a dual-functional ionic liquid

N,N,N’,N’-tetramethyl-N,N’-bis(sulfo)ethane-1,2-diaminium mesylate ([TMBSED][OMs]2) was employed for the synthesis of piperidines and dihydropyrrol-2-ones via one-pot multi-component reactions in simple and green processes. This pseudo five-component reaction of aromatic aldehydes, anilines and alkyl acetoacetates was carried out under reflux conditions in ethanol to afford substituted piperidines. Also, dihydropyrrol-2-one derivatives were synthesized by means of four-component reactions of various amines, dialkyl acetylenedicarboxylates and formaldehyde in ethanol at room temperature. The present approaches have several advantages such as good yields, easy work-ups, short reaction times, and utilize mild and clean reaction conditions.

Glutamic acid as green and bio-based α-amino acid catalyst promoted one-pot access to polyfunctionalized dihydro-2-oxypyrroles

A highly versatile and convenient synthetic route for biologically active α-amino acid, glutamic acid catalyzed facile and mild preparation of polyfunctionalized dihydro-2-oxypyrroles via one-pot, four condensation domino reaction between aromatic/aliphatic amines, dialkyl acetylenedicarboxylates and formaldehyde have been studied. The route includes green, biodegradable and inexpensive α-amino acid catalyst, high atom-economy, simplicity of operation and work-up procedures, without chromatographic purification steps. The solid catalyst, non-toxic or hazardous, easily handled with mild reaction conditions and excellent yields are the notable benefits of the highly efficient and expedient synthesis of these products.

Caffeine as a naturally green and biodegradable catalyst promoted convenient and expedient synthetic route for the synthesis of polysubstituted dihydro-2-oxypyrroles

A green, convenient, high yielding and one-pot procedure for synthesis of high substituted dihydro-2-oxypyrroles by domino four-component condensation reaction between aromatic/aliphatic amines, dialkyl acetylenedicarboxylate and formaldehyde in the presence of a catalytic amount of caffeine as a green, natural, expedient and biodegradable catalyst under ambient temperature was studied. The salient features of this green approach are simplicity of operation and work-up procedures with no necessity of chromatographic purification steps, use of safe, non-volatile, non-corrosive and green catalyst, the availability and easy to handle of this solid catalyst, one-pot reaction, economical and clean synthesis.

Application and developing of iron-doped multi-walled carbon nanotubes (Fe/MWCNTs) as an efficient and reusable heterogeneous nanocatalyst in the synthesis of heterocyclic compounds

Iron-doped multi-walled carbon nanotubes (Fe/MWCNTs) is an efficient, ecofriendly and reusable heterogeneous nanocatalyst for the one-pot synthesis of heterocyclic compounds including bis-spiro piperidines, piperidines, dihydro-2-oxopyrroles, pyrazoles and diazepines at room temperature with good to excellent yields. The heterogeneous nanocatalyst was fully characterized by scanning electron microscopy (SEM), X-ray diffraction (XRD), inductively coupled plasma (ICP) and FT-IR analysis. Also, the structures of all prepared compounds were characterized by 1H NMR, 13C NMR, FT-IR, mass spectrometry (MS) and elemental analysis. The major advantages of these protocols are mild and green reaction conditions, short reaction times, clean reaction, operational simplicity, easy purification and good to excellent yields with the reusable heterogeneous nanocatalyst. The catalyst was ten recycled without significant loss of activity.

Trifluoroacetic acid catalyzed one-pot four-component domino reaction for the synthesis of substituted dihydro 2-oxypyrroles

Trifluoroacetic acid was applied as an effcient catalyst for the one-pot four-component synthesis of N-aryl/alkyl-3-aminodihydropyrrol-2-one-4-carboxylates via the domino reaction of amines, formaldehyde and dialkyl acetylenedicarboxylates at ambient temp

Phthalic acid: A green, biodegradable and environmentally benign nature difunctional Br?nsted acid catalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-one derivatives and substituted dihydro-2-oxypyrroles

Phthalic acid as a green, biodegradable economical and environmentally benign nature catalyst for the one-pot three-component Biginelli synthesis of 3,4-dihydropyrimidin-2-(1H)-one derivatives via β-keto esters, aldehyde derivatives and urea/thiourea under thermal and solvent-free conditions and one-pot four-component domino condensation of substituted dihydro-2-oxypyrrole by reaction of dialkyl acetylenedicarboxylate, formaldehyde and amines (aromatic and aliphatic) under ambient temperature with short reaction times and excellent yields is reported. The most benefits this procedure are such as green, biodegradable, inexpensive and non-toxic catalyst, eco-friendly, high catalytic activity, efficient, easily separation with no column chromatographic separation, simple operational procedures, one-pot, excellent yields, environmentally benign nature.

Pectin; hetero polysaccharide as a green and natural catalyst for the synthesis of dihydro-2-oxopyrroles and 3,4,5-trisubstituted furan-2(5H)-ones

Use of green and biodegradable catalyst in organic synthesis is undeniable. Easy access, inexpensive, natural and green catalysts are valuable. In this study, a green procedure by using pectin as a green and natural catalyst for the one-pot synthesis of dihydro-2-oxopyrroles and 3,4,5-trisubstituted furan-2(5H)-ones at ambient temperature in aqueous media has been developed. This methodology has some advantages such as: use of a hetero polysaccharide as a easy access and biodegradable catalyst, clean work-up and no need to column chromatography.

Magnetic Metal-Organic Framework CoFe2O4@SiO2@IRMOF-3 as an Efficient Catalyst for One-Pot Synthesis of Functionalized Dihydro-2-oxopyrroles

A magnetic metal-organic framework-based catalyst CoFe2O4@SiO2@IRMOF-3 was prepared and identified as an efficient catalyst for the synthesis of a variety of functionalized dihydro-2-oxopyrroles by a one-pot, four-component reaction of a dialkyl acetylenedicarboxylate, an aryl amine, formaldehyde, and optionally a second amine or diamine at room temperature. The catalyst was magnetically separated and recovered without significant loss of its catalytic efficiency, even after eight reaction cycles.

Saccharin: a green, economical and efficient catalyst for the one-pot, multi-component synthesis of 3,4-dihydropyrimidin-2-(1H)-one derivatives and 1H-pyrazolo [1,2-b] phthalazine-5,10-dione derivatives and substituted dihydro-2-oxypyrrole

Abstract: In this method, we have reported the catalytic ability of saccharin as a green, eco-friendly catalyst for the multi-component efficient synthesis of 3,4-dihydropyrimidin-2-(1H)-one derivatives and 1H-pyrazolo [1,2-b]phthalazine-5,10-dione derivatives and substituted dihydro-2-oxypyrrole with excellent yields and short reaction times. This present methodology has notable benefits such as green, inexpensive and non-toxic catalyst, one-pot, environmental benign nature, solvent-free conditions, simplicity of operation with no necessity of chromatographic purification steps and eco-friendly. Graphical Abstract: We have studied the catalytic ability of saccharin as a green, economical and environmentally benign nature for the multi-component efficient synthesis of 3,4-dihydropyrimidin-2-(1H)-ones derivatives, 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives and substituted dihydro-2-oxypyrrole with excellent yields and short reaction times. Green catalyst, mild, non-toxic, inexpensive, simple operational procedures, one-pot, high catalytic activity, eco-friendly, easily separated from the reaction mixture with no column chromatographic for the one-pot multi-component synthesis of these compounds are the most important advantages of this procedure.[Figure not available: see fulltext.]