121-95-9

Usage

Uses

Used in Pharmaceutical Synthesis:
N-methyl-N-(4-nitrophenyl)acetamide is used as an intermediate in the synthesis of various drugs and pharmaceutical compounds. Its primary application is in the production of analgesic and anti-inflammatory medications, where it serves as a key component in the development of these therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, N-methyl-N-(4-nitrophenyl)acetamide is employed as a building block for the creation of a range of organic compounds. Its versatile structure allows for its incorporation into various chemical reactions, contributing to the synthesis of different organic molecules with potential applications in various industries.

InChI:InChI=1/C9H10N2O3/c1-7(12)10(2)8-3-5-9(6-4-8)11(13)14/h3-6H,1-2H3

Upstream product

• 579-10-2 N-acetyl-N-methylaniline 
• 108-24-7 acetic anhydride 
• 100-15-2 N-methyl(p-nitroaniline) 
• 100-23-2 N,N-Dimethyl-4-nitroaniline 
• 104-04-1 N-(4-Nitrophenyl)acetamide 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 
• 100-61-8 N-methylaniline 
• 75-36-5 acetyl chloride 
• 80-43-3 bis(1-methyl-1-phenylethyl)peroxide 

Downstream Products

• 943-41-9 N-methyl-N-nitroso-4-nitroaniline 
• 2044-88-4 N-methyl-2,4-dinitroaniline 
• 99071-56-4 N-(4-cyanophenyl)-N-methylacetamide 
• 4714-62-9 4-cyano-N-methylaniline 
• 114224-23-6 1,3-bis-[4-(N-methyl-acetylamino)-phenyl]-triazene 
• 806632-62-2 4-methylamino-benzamidine 
• 65052-84-8 N-Methyl-4-nitro-thioacetanilid 
• 100-15-2 N-methyl(p-nitroaniline) 
• 119-63-1 4-(N-methylacetamido)aniline 

Relevant academic research and scientific papers

Regioselective nitration of anilines with Fe(NO3)3·9H2O as a promoter and a nitro source

An efficient Fe(NO3)3·9H2O promoted ortho-nitration reaction of aniline derivatives has been developed. This reaction may go through a nitrogen dioxide radical (NO2) intermediate, which is generated by the thermal decomposition of iron(iii) nitrate. The practicality of the present method using nontoxic and inexpensive iron reagents has been shown by the broad substrate scope and applications.

The copper-catalyzed aerobic oxidative amidation of tertiary amines

A general and efficient method for the synthesis of tertiary amides has been developed via the copper-catalyzed aerobic oxidative amidation of tertiary amines. Due to the use of the O2 oxidant, various functional groups were well tolerated under the present conditions. Extensive substrates studies demonstrated its potential as a practical approach for the synthesis of tertiary amides.

Copper-catalyzed N-methylation of amides and O-methylation of carboxylic acids by using peroxides as the methylating reagents

The copper-catalyzed N-methylation of amides and O-methylation of carboxylic acids by using peroxides as the methylating reagent are described. Various amides and carboxylic acids were methylated affording N-substituted amides and esters. Tentative mechanistic studies suggest that this reaction is likely to involve a radical process.

Regioselective ortho-nitration of N-phenyl carboxamides and primary anilines using bismuth nitrate/acetic anhydride

An efficient and one-pot synthetic method for the regioselective ortho-nitration of the N-phenyl carboxamides and primary anilines has been developed by using bismuth nitrate and acetic anhydride as the nitrating reagents. Reaction proceeds at room temperature and results in corresponding ortho-nitrated products in moderate to excellent yields. This method provides an operationally simple, regioselective, and efficient access to synthesize o-nitro anilines under the mild conditions.

Substituted Isoquinolinones and Quinazolinones

The invention relates to substituted nitrogen containing bicyclic heterocycles of the formula (I) wherein Z is CH2 or N—R4 and X, R1, R2, R4, R6, R7 and n are as defined in the description. Such compounds are suitable for the treatment of a disorder or disease which is mediated by the activity of MDM2 and/or MDM4, or variants thereof.

Oligo(N-aryl glycines): A new twist on structured peptoids

We explore strategies to enhance conformational ordering of N-substituted glycine peptoid oligomers. Peptoids bearing bulky N-alkyl side chains have previously been studied as important examples of biomimetic "foldamer" compounds, as they exhibit a capacity to populate helical structures featuring repeating cis-amide bonds. Substantial cis/trans amide bond isomerization, however, gives rise to conformational heterogeneity. Here, we report the use of N-aryl side chains as a tool to enforce the presence of trans-amide bonds, thereby engendering structural stability. Aniline derivatives and bromoacetic acid are used in the facile solid-phase synthesis of a diverse family of sequence-specific N-aryl glycine oligomers. Quantum mechanics calculations yield a detailed energy profile of the folding landscape and substantiate the hypothesis that the presence of anilide groups establishes a strong energetic preference for trans-amide bonds. X-ray crystallographic analysis and solution NMR studies verify this preference. Molecular modeling indicates that the linear oligomers can adopt helical structures resembling a polyproline type II helix. High resolution structures of macrocyclic oligomers incorporating both N-alkyl and N-aryl glycine units confirm the ability to direct the presence of trans-amide bonds specifically at N-aryl positions. These results are an important step in developing strategies for the rational de novo design of new structural motifs in biomimetic oligopeptoid systems.

AMIDE COMPOUND

There is provided a FAAH inhibitor and a prophylactic or therapeutic agent for cerebrovascular disorders or sleep disorders comprising it. The prophylactic or therapeutic agent comprises a compound of the formula (I0): wherein Z is oxygen or sulfur; R1 is aryl which may be substituted, or a heterocyclic group which may be substituted; R1a is a hydrogen atom, a hydrocarbon group which may be substituted, hydroxyl, etc.; R2 is piperidin-1,4-diyl which may be substituted, or piperazin-1,4-diyl which may be substituted; R3 is a group formed by eliminating two hydrogen atoms from a 5-membered aromatic heterocyclic group having 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur, which may be further substituted, -CO-, etc.; and R4 is a hydrocarbon group which may be substituted, or a heterocyclic group which may be substituted; or a salt thereof.

Amide conformational switching induced by protonation of aromatic substituent

(Matrix presented) Introduction of an electron-withdrawing group on the aromatic ring of N-methylacetanilide decreased the ratio of the cis conformer, and the ratio correlates well with the Hammett σ values of the substituents. These steric properties can be applied to achieve amide conformational swiching by protonation at the aromatic substituent of 4-[bis(dimethylamino)]-N-methylacetanilide or N-[p-(dimethylamino)phenyl]-N-phenylacetamide.

Ozone-mediated Reaction of Anilides and Phenyl Esters with Nitrogen Dioxide: Enhanced Ortho-reactivity and Mechanistic Implications

In the presence of ozone, anilides 1 can be nitrated rapidly with nitrogen dioxide in chloroform at 0 deg C to give a high proportion of ortho-nitro derivatives (ortho:para = 1.2-4.4) in good yields.The phenyl esters 15 can be similarly nitrated on the aromatic ring without significant cleavage of the ester bond, giving a mixture of isomeric nitro derivatives in which the ortho-isomer predominantes (ortho:para = 1.1-1.5).The oridin of the enhanced ortho reactivity is discussed in terms of an electron-transfer process involving the nitrogen trioxide as initial electrophile.