1132-03-2

Basic information

• Product Name: 2-(hydroxyimino)-N-(2-methylphenyl)acetamide
• Synonyms: 2-(hydroxyimino)-N-(2-methylphenyl)acetamide;Nsc20557;(2E)-2-(Hydroxyimino)-N-(2-methylphenyl)acetamide;AcetaMide, 2-(hydroxyiMino)-N-(2-Methylphenyl)-
• CAS NO: 1132-03-2
• Molecular Formula: C₉H₁₀N₂O₂
• Molecular Weight: 178.1879
• EINECS: 214-472-2
• Mol File: 1132-03-2.mol

Chemical Properties

• Appearance: /
• Density: 1.17g/cm³
• Refractive Index: 1.559
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(hydroxyimino)-N-(2-methylphenyl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(hydroxyimino)-N-(2-methylphenyl)acetamide(1132-03-2)
• EPA Substance Registry System: 2-(hydroxyimino)-N-(2-methylphenyl)acetamide(1132-03-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 1132-03-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
2-(hydroxyimino)-N-(2-methylphenyl)acetamide is used as a research intermediate for the development of new pharmaceutical compounds, leveraging its unique structural features to contribute to the synthesis of novel drugs.
Used in Agrochemical Compounds:
In the agrochemical industry, 2-(hydroxyimino)-N-(2-methylphenyl)acetamide is used as an intermediate in the preparation of various agrochemicals, potentially enhancing crop protection and yield through its incorporation into effective formulations.
Used in Organic Synthesis:
As a component in organic synthesis, 2-(hydroxyimino)-N-(2-methylphenyl)acetamide is employed as a building block for the creation of complex organic molecules, contributing to the advancement of chemical libraries and the discovery of new chemical entities.
Used in Medicinal Chemistry for Antimicrobial Properties:
2-(hydroxyimino)-N-(2-methylphenyl)acetamide is studied for its potential antimicrobial properties, making it a candidate for use in the development of new antimicrobial agents to combat resistant strains of bacteria.
Used in Medicinal Chemistry for Antioxidant Properties:
2-(hydroxyimino)-N-(2-methylphenyl)acetamide is also of interest in medicinal chemistry due to its antioxidant potential, which could be harnessed in the formulation of therapeutics aimed at treating conditions associated with oxidative stress.

InChI:InChI=1/C9H10N2O2/c1-7-4-2-3-5-8(7)11-9(12)6-10-13/h2-6,13H,1H3,(H,11,12)/b10-6+

Upstream product

• 95-53-4 o-toluidine 
• 515-83-3 chloral ethyl hemiacetal 
• 75-87-6 chloral 
• 302-17-0 chloral hydrate 

Downstream Products

• 1217506-70-1 3-(allyloxy)-N-(4-chloro-2-methyl-6-(propylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide 
• 1217506-71-2 3-(allyloxy)-N-(2-(butylcarbamoyl)-4-chloro-6-methylphenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide 
• 1217506-72-3 3-(allyloxy)-N-(4-chloro-2-(isobutylcarbamoyl)-6-methylphenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide 
• 1217506-73-4 3-(allyloxy)-N-(4-chloro-2-(cyclohexylcarbamoyl)-6-methylphenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide 
• 1217506-79-0 3-(allyloxy)-1-(3-chloropyridin-2-yl)-N-(2-methyl-6-(propylcarbamoyl)phenyl)-1H-pyrazole-5-carboxamide 
• 1217506-80-3 3-(allyloxy)-1-(3-chloropyridin-2-yl)-N-(2-(isopropylcarbamoyl)-6-methylphenyl)-1H-pyrazole-5-carboxamide 
• 1217506-81-4 3-(allyloxy)-1-(3-chloropyridin-2-yl)-N-(2-(cyclopropylcarbamoyl)-6-methylphenyl)-1H-pyrazole-5-carboxamide 
• 1127-59-9 7-methyl-1H-indole-2,3-dione 
• 13208-93-0 N-(4-chloro-2-methylphenyl)-2-(hydroxyimino)acetamide 
• 84902-24-9 2-amino-3-methylbenzaldehyde 
• 57772-50-6 2-amino-3-methylbenzyl alcohol 
• 91790-39-5 N,7-dimethylindoline-2,3-dione 
• 67358-21-8 1,7-dimethylindolin-2-one 
• 620931-90-0 1-benzyl-7-methylindoline-2,3-dione 

Relevant articles and documents

Study on synthesis of some substituted N-propargyl isatins by propargylation reaction of corresponding isatins using potassium carbonate as base under ultrasound- and microwave-assisted conditions

Substituted N-propargyl isatins were synthesized by SN2 reaction of corresponding substituted isatins with propargyl bromide in the presence of anhydrous K2CO3 as base. We reported about study on systematically synthesis of these compounds using heating procedures under different reaction conditions, including microwave-assisted heating conditions at power of 100?W (Procedure A), conventional heating conditions in water bath at 50?°C in acetonitrile (Procedure B), and conventional heating conditions in water bath at 50?°C in DMF (procedure C). The best procedure A was deduced based on the investigations on the reaction conditions. Almost all substituted N-propargyl isatins were new, except compounds with R of H, 5-Me, 5-Cl and 5-Br substituents. The structures of the obtained compounds were confirmed by the modern spectroscopic methods.

Synthesis process of 2-amino-5-chloro-3-methylbenzoic acid intermediate 2-(hydroxyimino)-N-(2-methylphenyl)acetamide

The invention discloses a novel process for synthesizing a 2-amino-5-chloro-3-methylbenzoic acid intermediate, namely 2-(hydroxyimino)-N-(2-methylphenyl)acetamide. According to the process, o-aminotoluene is used as a main starting raw material, and synthesis of 2-(hydroxyimino)-N-(2-methylphenyl)acetamide is realized through two steps including amino acetylation and oximation. Compared with the prior art, the process of the invention has the advantages that product yield reaches 97% or above, the generation of waste salt sodium chloride and sodium sulfate is reduced by three times or above, intermediate raw materials are low in price, process is simple, cost is reduced, and environmental and economic benefits are improved.

A PROCESS FOR PREPARING ANTHRANILIC DIAMIDES AND INTERMEDIATES THEREOF

The present invention relates a novel process for preparing a compound of Formula I, wherein, R1, R2, R3a, R3b, R3c, R4, R5, R6, R7 and Z are as defined in the description. The process comprises a novel and inventive step of converting a dione of Formula II into an isatoic anhydride of Formula V in a single step, wherein, R2 is F, Cl, Br or I; R1, R3a, R3b, R3c, R4, R5, R6, R7 and Z are as defined in the description.

Design and development of Isatin-triazole hydrazones as potential inhibitors of microtubule affinity-regulating kinase 4 for the therapeutic management of cell proliferation and metastasis

Microtubule affinity-regulating kinase 4 (MARK4) is a potential drug target as the same is found to be over expressed in several types of cancers. In search of effective MARK4 inhibitors, we have synthesized and characterized Isatin-triazole hydrazones (9a-i) and evaluated their inhibitory potential. Of all the compounds, 9g showed better binding affinity and enzyme inhibition potential in sub micromolar range. Human serum albumin (HSA) binding assay suggested an easy transportation of 9g in blood stream due to its binding affinity. In vitro anticancer studies performed on MCF-7, MDA-MB-435s and HepG2 cells using 9g showed inhibition of cell proliferation and cell migration. Further, 9g induces apoptosis in these cancerous cells, with IC50 values of 6.22, 9.94 and 8.14 μM, respectively. Putatively, 9g seems to cause oxidative stress resulting in apoptosis. Functional assay of 9g with a panel of 26 kinases showed MARK4 specific profile. In conclusion, 9g seems to possess an effective inhibitory potential towards MARK4 adding an additional repertoire to anticancer therapeutics.

Enantioselective synthesis of tunable chiral pyridine-aminophosphine ligands and their applications in asymmetric hydrogenation

A small library of tunable chiral pyridine-aminophosphine ligands were enantioselectively synthesized based on chiral 2-(pyridin-2-yl)-substituted 1,2,3,4-tetrahydroquinoline scaffolds, which were obtained in high yields and with excellent enantioselectivities via ruthenium-catalyzed asymmetric hydrogenation of 2-(pyridin-2-yl)quinolines. The protocol features a wide substrate scope and mild reaction conditions, enabling scalable synthesis. These chiral P,N ligands were successfully applied in the Ir-catalyzed asymmetric hydrogenation of benchmark olefins and challenging seven-membered cyclic imines including benzazepines and benzodiazepines. Excellent enantio- and diastereoselectivity (up to 99% ee and >20:1 dr), and/or unprecedented chemoselectivity were obtained in the asymmetric hydrogenation of 2,4-diaryl-3H-benzo[b]azepines and 2,4-diaryl-3H-benzo[b][1,4]diazepines.

Palladium(II)/N-Heterocyclic Carbene Catalyzed One-Pot Sequential α-Arylation/Alkylation: Access to 3,3-Disubstituted Oxindoles

Rationally designed fluorene-based mono- and bimetallic Pd-PEPPSI complexes were synthesized and demonstrated to be effective for the one-pot sequential α-arylation/alkylation of oxindoles. This streamlined approach offers efficient access to functionalized 3,3-disubstituted oxindoles in excellent yields (up to 89%) under mild reaction conditions.

Isatin N,N′-Cyclic Azomethine Imine 1,3-Dipole and Abnormal [3 + 2]-Cycloaddition with Maleimide in the Presence of 1,4-Diazabicyclo[2.2.2]octane

A new isatin N,N′-cyclic azomethine imine synthon was devised, and an unexpected abnormal [3 + 2]-cycloaddition with maleimide catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO) has been disclosed. A variety of tricyclic spiropyrrolidine oxindoles bearing a dinitrogen heterocycle and succinimide scaffold were obtained in excellent yields (up to 96%) and diastereoselectivities (up to 97:3) under mild conditions.

Combretastatin A-4 analogues with benzoxazolone scaffold: Synthesis, structure and biological activity

In order to design and synthesize a new class of heterocyclic analogues of natural combretastatin A-4 and its synthetic derivative AVE8062, the benzoxazolone ring was selected as a scaffold for a bioisosteric replacement of the ring B of both molecules. A library of 28 cis- and trans-styrylbenzoxazolones was obtained by a modified Wittig reaction under Boden's conditions. Structures of the newly synthesized compounds bearing the 3,4,5-trimethoxy-, 3,4-dimethoxy-, 3,5-dimethoxy-, and 4-methoxystyryl fragment at position 4, 5, 6 or 7 of benzoxazolone core were determined on the basis of spectral and X ray data. The in vitro cytotoxicity of styrylbenzoxazolones against different cell lines was examined. Stilbene derivative 16Z, (Z)-3-methyl-6-(3,4,5-trimethoxystyryl)-2(3H)-benzoxazolone, showed highest antiproliferative potential of the series, with IC50 of 0.25 μM against combretastatin resistant cell line HT-29, 0.19 μM against HepG2, 0.28 μM against EA.hy926 and 0.73 μM against K562 cells. Furthermore, the results of flow cytometric analysis confirmed that 16Z induced cell cycle arrest in G2/M phase in the cell lines like combretastatin A-4. This arrest is followed by an abnormal exit of cells from mitosis without cytokinesis into a pseudo G1-like multinucleate state leading to late apoptosis and cell death. Accordingly, synthetic analogue 16Z was identified as the most promising potential anticancer agent in present study, and was selected as lead compound for further detailed investigations.

Synthesis, Crystal Structure, and Biological Activity of Novel Anthranilic Diamide Insecticide Containing Propargyl Ether Group

In search of environmentally benign insecticides with high activity, low toxicity, and low residue, a series of novel anthranilic diamide containing propargyl ether were designed and synthesized. All compounds were characterized by1H NMR spectroscopy, high-resolution mass spectrometry, or elemental analysis. The single crystal structure of 18g was determined by X-ray diffraction. The insecticidal activities against Lepidoptera pests of the new compounds were evaluated. Their insecticidal activities against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella) indicated that most of the compounds showed moderate to high activities at the tested concentration.

Synthesis and pharmacological evaluation of N-benzyl substituted 4-bromo-2,5-dimethoxyphenethylamines as 5-HT2A/2C partial agonists

N-Benzyl substitution of phenethylamine 5-HT2A receptor agonists has dramatic effects on binding affinity, receptor selectivity and agonist activity. In this paper we examine how affinity for the 5-HT2A/2C receptors are influenced by N-benzyl substitution of 4-bromo-2,5-dimethoxyphenethylamine derivatives. Special attention is given to the 2′ and 3′-position of the N-benzyl as such compounds are known to be very potent. We found that substitutions in these positions are generally well tolerated. The 2′-position was further examined using a range of substituents to probe the hydrogen bonding requirements for optimal affinity and selectivity, and it was found that small changes in the ligands in this area had a profound effect on their affinities. Furthermore, two ligands that lack a 2′-benzyl substituent were also found to have high affinity contradicting previous held notions. Several high-affinity ligands were identified and assayed for functional activity at the 5-HT2A and 5-HT2C receptor, and they were generally found to be less efficacious agonists than previously reported N-benzyl phenethylamines.