53578-11-3

Usage

Uses

Used in Pharmaceutical Industry:
4-Nitro-1-(pyrrolidinocarbonyl)benzene is used as a starting material for the synthesis of various drugs and pharmaceutical compounds. Its unique chemical structure allows for the development of new and innovative medications.
Used in Research Laboratories:
NPCB is used as a reagent for the modification of proteins and peptides. Its ability to interact with these biomolecules makes it a valuable tool in scientific research for studying protein structure, function, and interactions.
However, it is important to note that 4-Nitro-1-(pyrrolidinocarbonyl)benzene is toxic and potentially harmful if ingested or inhaled. Therefore, it should be handled with care and proper safety precautions should be taken during its use.

Upstream product

• 123-75-1 pyrrolidine 
• 619-50-1 4-nitrobenzoic acid methyl ester 
• 4231-71-4 1H-1,2,3-benzotriazol-1-yl-4-nitrophenylmethanone 
• 122-04-3 4-nitro-benzoyl chloride 
• 555-16-8 4-nitrobenzaldehdye 
• 636-98-6 p-nitrobenzene iodide 
• 201230-82-2 carbon monoxide 
• 30364-58-0 p-nitrobenzoic acid N-hydroxysuccinimide ester 
• 13939-06-5 molybdenum hexacarbonyl 
• 25407-30-1 4-nitrophenacylpyridinium bromide 
• 2564-83-2 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical 
• 128-37-0 2,6-di-tert-butyl-4-methyl-phenol 
• 99-99-0 1-methyl-4-nitrobenzene 
• 619-73-8 4-nitrobenzyl chloride 

Downstream Products

• 119741-53-6 1-(4-nitrobenzoyl)pyrrolidin-2-one 
• 56302-41-1 4-carboxamidopyrrolidinophenyl-aniline 
• 877603-33-3 4-(pyrrolidinylcarbonyl)phenylamine hydrochloride 
• 50903-06-5 (4-nitrophenyl)(pyrrolidin-1yl)methanethione 
• 694-00-8 pyrrolidine-1-d₁ 
• 2906-29-8 4-nitrobenzoate 
• 133851-67-9 1-(4-nitro-benzyl)-pyrrolidine 
• 1019018-76-8 (4-amino-3-bromo-phenyl)-pyrrolidin-1-yl-methanone 

Relevant academic research and scientific papers

Visible-Light-Mediated Oxidative Amidation of Aldehydes by Using Magnetic CdS Quantum Dots as a Photocatalyst

A magnetic CdS quantum dot (Fe3O4/polydopamine (PDA)/CdS) was synthesized through a facile and convenient method from inexpensive starting materials. Characterization of the prepared catalyst was performed by means of FTIR spectrosco

Photocatalytic aldehydes/alcohols/toluenes oxidative amidation over bifunctional Pd/MOFs: Effect of Fe-O clusters and Lewis acid sites

Heterogeneous photocatalytic organic synthesis is fascinating because of the utilization of ubiquitous solar light for chemical transformations. Here, three Fe-MOFs with different Fe-O clusters, Lewis acid sites and morphologies were synthesized through coordination structure engineering. Pd/Fe-MOFs nanocomposites were used to challenge the amide bond green synthesis with visible light. Pd/MIL-101(Fe) exhibited the best photocatalytic performance due to the easily excited Fe3-μ3-oxo clusters for light absorption, the efficient photogenerated carriers separation and migration, the large amount of Lewis acid sites based aldehydes and amines condensation promotion and the efficient O2 reduction to superoxide radicals over photogenerated electron-rich Pd NPs. Various aldehydes, alcohols and toluenes could be transformed to amide compounds with amines over Pd/MIL-101(Fe) with just oxygen or air as the green oxidant and water as the by-product. One-pot C–C cross-coupling and photo-redox C–N coupling cascade reactions could also be achieved over Pd/MIL-101(Fe). This work shed light on the efficient and sustainable amide bonds synthesis.

Amide Bond Formation via Aerobic Photooxidative Coupling of Aldehydes with Amines Catalyzed by a Riboflavin Derivative

We report an effective, operationally simple, and environmentally friendly system for the synthesis of tertiary amides by the oxidative coupling of aromatic or aliphatic aldehydes with amines mediated by riboflavin tetraacetate (RFTA), an inexpensive organic photocatalyst, and visible light using oxygen as the sole oxidant. The method is based on the oxidative power of an excited flavin catalyst and the relatively low oxidation potential of the hemiaminal formed by amine to aldehyde addition.

Visible-Light-Driven C-N Bond Formation by a Hexanickel Cluster Substituted Polyoxometalate-Based Photocatalyst

A powerful and attractive route to develop novel photocatalysts for C-N bond formation involves the use of pyrrolidine as the substrate and cocatalyst simultaneously. Herein, a new polyoxometalate (POM)-based metal-organic framework, namely, [Ni6(OH)3(H2O

A practical catalytic reductive amination of carboxylic acids

We report reductive alkylation reactions of amines using carboxylic acids as nominal electrophiles. The two-step reaction exploits the dual reactivity of phenylsilane and involves a silane-mediated amidation followed by a Zn(OAc)2-catalyzed amide reduction. The reaction is applicable to a wide range of amines and carboxylic acids and has been demonstrated on a large scale (305 mmol of amine). The rate differential between the reduction of tertiary and secondary amide intermediates is exemplified in a convergent synthesis of the antiretroviral medicine maraviroc. Mechanistic studies demonstrate that a residual 0.5 equivalents of carboxylic acid from the amidation step is responsible for the generation of silane reductants with augmented reactivity, which allow secondary amides, previously unreactive in zinc/phenylsilane systems, to be reduced.

A metal-free approach for the synthesis of amides/esters with pyridinium salts of phenacyl bromides via oxidative C–C bond cleavage

An efficient, simple, and metal-free synthetic approach for the N- and O-benzoylation of various amines/benzyl alcohols with pyridinium salts of phenacyl bromides is demonstrated to generate the corresponding amides and esters. This protocol facilitates the oxidative cleavage of a C–C bond followed by formation of a new C–N/C–O bond in the presence of K2CO3. Various pyridinium salts of phenacyl bromides can be readily transformed into a variety of amides and esters which is an alternative method for the conventional amidation and esterification in organic synthesis. High functional group tolerance, broad substrate scope and operational simplicity are the prominent advantages of the current protocol.

Oxidative amidation of benzaldehyde using a quinone/DMSO system as the oxidizing agent

An efficient transition-metal-based heterogeneous catalyst free procedure for obtaining the oxidative amidation of benzaldehyde using quinones as oxidizing agents in low molar proportions is described here. Pyrrolylquinones (PQ) proved to be more suitable

Design, synthesis and biological evaluation of novel 2-phenyl pyrimidine derivatives as potent Bruton's tyrosine kinase (BTK) inhibitors

BTK is an effective target for the treatment of B-cell malignant tumors and autoimmune diseases. In this work, a series of 2-phenyl pyrimidine derivatives were prepared and their preliminary in vitro activities on B-cell leukemia cells as well as the BTK enzyme were determined. The results showed that compound 11g displayed the best inhibitory activity on BTK with an inhibition rate of 82.76% at 100 nM and excellent anti-proliferation activity on three B-cell leukemia lines (IC50 = 3.66 μM, 6.98 μM, and 5.39 μM against HL60, Raji and Ramos, respectively). Besides, the flow cytometry analysis results indicated that 11g inhibited the proliferation of the Raji cells in a dose- and time-dependent manner, and blocked the Ramos cells at the G0/G1 phase, which is in accordance with the positive control ibrutinib. The mechanism investigation demonstrated that 11g could inhibit the phosphorylation of BTK and its downstream substrate phospholipase γ2 (PLCγ2). All these results showed that 11g was a promising lead compound that merited further optimization as a novel class of BTK inhibitor for the treatment of B-cell lymphoblastic leukemia.

Method for synthesizing amide compounds by using N-Boc amide as substrate

The invention relates to a method for synthesizing amide compounds by using N-Boc amide as a substrate. According to the method, N-Boc amide and various amine compounds are subjected to an intermolecular nucleophilic substitution reaction in an organic solvent so as to efficiently prepare various amide compounds. The method has the advantages of mild reaction conditions, simple and convenient operation, high yield and good functional group compatibility.

Broadly Applicable Ytterbium-Catalyzed Esterification, Hydrolysis, and Amidation of Imides

An efficient, broadly applicable, operationally simple, and divergent process for the transformation of imides into a range of carboxylic acid derivatives under mild conditions is reported. By simply using catalytic amounts of ytterbium(III) triflate as a Lewis acid promoter in the presence of alcohols, water, amines, or N,O-dimethylhydroxylamine, a broad range of imides is smoothly and readily converted to the corresponding esters, carboxylic acids, amides, and Weinreb amides in good yields. This method notably enables an easy cleavage of oxazolidinone-based auxiliaries.