93-27-6

Usage

Uses

Used in Pharmaceutical Industry:
N-(2-Methoxy-4-nitrophenyl)acetamide is used as an intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and improving existing ones. Its unique chemical structure allows it to be a versatile building block in drug production.
Used in Chemical Industry:
In the chemical industry, N-(2-Methoxy-4-nitrophenyl)acetamide is utilized in the synthesis of various organic compounds, expanding the range of chemical products and enabling the creation of new materials with specific properties.
Used in Research:
N-(2-Methoxy-4-nitrophenyl)acetamide is employed in research settings for the study of chemical reactions and the development of new synthetic pathways. Its unique properties make it a valuable tool for understanding and advancing the field of organic chemistry.

InChI:InChI=1/C9H10N2O4/c1-6(12)10-8-4-3-7(11(13)14)5-9(8)15-2/h3-5H,1-2H3,(H,10,12)

Upstream product

• 93-26-5 2-methoxyacetanilide 
• 108-24-7 acetic anhydride 
• 90-04-0 2-methoxy-phenylamine 
• 25351-89-7 N-(2-hydroxy-4-nitrophenyl)acetamide 
• 77-78-1 dimethyl sulfate 
• 75-36-5 acetyl chloride 
• 97-52-9 2-methoxy-4-nitrophenylamine 
• 7697-37-2 nitric acid 
• 3962-77-4 2,5-dinitro-anisole 

Downstream Products

• 83209-82-9 N-<2-methoxy-4-<(methylsulfonyl)amino>phenyl>acetamide 
• 106994-15-4 N-(4-amino-5-methoxy-2-nitrophenyl)-N-(2-propenyl)methanesulfonamide 
• 116911-55-8 N-(4-acetamido-5-mthoxy-2-nitrophenyl)methanesulfonamide 
• 116911-56-9 N-(4-acetamido-5-methoxy-2-nitrophenyl)-N-(2-propenyl)methanesulfonamide 
• 106994-16-5 2-methoxy-5-nitro-4-phenylhydrazone of ethyl 2-oxobutenoate 
• 116911-57-0 2-[4-(Allyl-methanesulfonyl-amino)-2-methoxy-5-nitro-phenylazo]-2-ethyl-3-oxo-butyric acid ethyl ester 
• 59557-91-4 4-bromo-2-methoxyaniline 
• 791642-68-7 4-bromo-1-iodo-2-methoxybenzene 
• 20278-59-5 4,5-dinitro-2-methoxyaniline 
• 106994-16-5 2-{[4-(Allyl-methanesulfonyl-amino)-2-methoxy-5-nitro-phenyl]-hydrazono}-butyric acid ethyl ester 
• 92138-16-4 9-(4-Methanesulfonylamino-2-methoxy-phenylamino)-5-methyl-acridine-4-carboxylic acid methylamide; hydrochloride 
• 57165-06-7 N-(4-amino-3-methoxyphenyl)methanesulfonamide 
• 87223-51-6 C₁₄H₁₈N₄O₆ 
• 15862-00-7 2-Methoxy-4-nitro-N-nitroso-acetanilid 

Relevant academic research and scientific papers

Continuous synthesis method 2 -acetylamino -5 - nitroanisole

The invention mainly relates to the field of organic synthesis, and discloses a continuous synthesis process for 2 -acetylamino -5 - nitroanisole. The process takes a microchannel continuous flow reactor as a main reaction device, and anthranilic acid is taken as a starting raw material and is subjected to preacylation. And nitration, a continuous synthesis 2 - acetylamino -5 - nitroanisole was achieved. To the process, the compound amidation reagent is adopted, the raw material cost is reduced, and the amidation reagent and the reaction solvent are unified. The continuous production process and equipment are introduced, continuous production is realized, the automation degree is improved, and the production safety risk is greatly reduced. The reaction time, the generation of by-products and the subsequent treatment difficulty are reduced, the nitration selectivity is improved, the economic benefits and environmental benefits are achieved, and the development concept of the green chemistry is met.

Method for continuously synthesizing 2 -methoxy -4 - nitroacetanilide

The invention provides a method for continuously synthesizing 2 - methoxy -4 - nitroacetanilide, the method is carried out in a microreactor, and an o-methoxyacetanilide solution and a nitration reagent are continuously subjected to nitration reaction through a microreactor. The nitration reagent is a mixed liquid of sodium metabisulfite and nitric acid, and sodium metabisulfite is formed in the nitration reaction process. Compared with the prior art, the molar ratio of nitric acid and o-methoxyacetanilide is 0.005 - 0.04: 1.0 - 3.0: 1.0 2 - the nitration reaction temperature is -4 - 0.5 - 3 min; and the nitration reaction temperature is 30 - 70 °C. and the process efficiency is remarkably improved compared with the prior art.

Preparation method of 2-methoxy-4-nitroaniline

The invention discloses a preparation method of 2-methoxy-4-nitroaniline. The preparation method comprises the following steps of: carrying out acetylation reaction of o-methoxyaniline and acetic acid, discharging water generated in the acetylation reaction process from a reaction system, dropwisely adding fuming nitric acid into the prepared acetic acid solution of the o-methoxyacetanilide to carry out nitration reaction, adding deionized water after the nitration reaction is finished and then filtering, adding the prepared 2-methoxy-4-nitroaniline into an alkali solution to carry out hydrolysis reaction; after the hydrolysis reaction is finished, cooling the prepared reaction solution, and filtering to obtain 2-methoxy-4-nitroaniline. By adopting the method to synthesize 2-methoxy-4-nitroaniline, the acylation reaction cost is low, the nitration reaction selectivity is high, the discharge of three wastes is reduced, the production cost is reduced, the product purity is high, the yield is high, and the 2-methoxy-4-nitroaniline has a good industrial application value.

Discovery of wtRET and V804MRET Inhibitors: From Hit to Lead

Oncogenic activation of RET kinase has been found in several neoplastic diseases, like medullary thyroid carcinoma, multiple endocrine neoplasia, papillary thyroid carcinoma, and non-small-cell lung cancer. Currently approved RET inhibitors were not originally designed to be RET inhibitors, and their potency against RET kinase has not been optimized. Hence, novel compounds able to inhibit both wild-type RET (wtRET) and its mutants (e.g., V804MRET) are needed. Herein we present the development and the preliminary evaluation of a new sub-micromolar wtRET/V804MRET inhibitor, N-(2-fluoro-5-trifluoromethylphenyl)-N′-{4′-[(2′′-benzamido)pyridin-4′′-ylamino]phenyl}urea (69), endowed with a 4-anilinopyridine structure, starting from our previously identified 4-anilinopyrimidine hit compound. Profiling against a panel of kinases indicated 69 as a multi cKIT/wtRET/V804MRET inhibitor.

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.

Ratiometric fluorescent sensor based on inhibition of resonance for detection of cadmium in aqueous solution and living cells

Although cadmium has been recognized as a highly toxic heavy metal and poses many detrimental effects on human health, the Cd2+-uptake and nosogenesis mechanisms are still insufficiently understood, mainly because of the lack of facile analytical methods for monitoring changes in the environmental and intracellular Cd2+ concentrations with high spatial and temporal reliability. To this end, we present the design, synthesis, and photophysical properties of a cadmium sensor, DQCd1 based on the fluorophore 4-isobutoxy-6-(dimethylamino)-8-methoxyquinaldine (model compound 1). Preliminary investigations indicate that 1 could be protonated under neutral media and yield a resonance process over the quinoline fluorophore. Upon excitation at 405 nm, 1 shows a strong fluorescence emission at 554 nm with a quantum yield of 0.17. Similarly, DQCd1 bears properties comparable to its precursor. It exhibits fluorescence emission at 558 nm (Φf = 0.15) originating from the monocationic species under physiological conditions. Coordination with Cd2+ causes quenching of the emission at 558 nm and simultaneously yields a significant hypsochromic shift of the emission maximum to 495 nm (Φf = 0.11) due to inhibition of the resonance process. Thus, a single-excitation, dual-emission ratiometric measurement with a large blue shift in emission (Δλ = 63 nm) and remarkable changes in the ratio (F495 nm495/F558 nm) of the emission intensity (R/R 0 up to 15-fold) is established. Moreover, the sensor DQCd1 exhibits very high sensitivity for Cd2+ (Kd = 41 pM) and excellent selectivity response for Cd2+ over other heavy- and transitionmetal ions and Na+, K+, Mg2+, and Ca2+ at the millimolar level. Therefore, DQCd1 can act as a ratiometric fluorescent sensor for Cd2+ through inhibition of the resonance process. Confocal microscopy and cytotoxicity experiments indicate that DQCd1 is cellpermeable and noncytotoxic under our experimental conditions. It can indeed visualize the changes of intracellular Cd2+ in living cells using dual-emission ratiometry.

Design and synthesis of anti-MRSA benzimidazolylbenzenesulfonamides. QSAR studies for prediction of antibacterial activity

A series of benzimidazolylbenzenesulfonamide compounds containing electronreleasing and electron-withdrawing substituents were synthesized and tested for their in vitro antibacterial activity. Two BZS compounds showed strong antibacterial activity against methicillin-resistant Staphylococcus aureus and Bacillus subtilis. Quantitative studies of their structure-activity relationship using a simple linear regression analysis were applied to explore the correlation between the biological activity and the charges on acidic hydrogen atoms in the synthesized compounds.

Synthesis of 2,1-benzisoxazoles by nucleophilic substitution of hydrogen in nitroarenes activated by the azole ring

Reaction of 1-nitro-4-(1,2,3-triazolyl/tetrazolyl)benzenes with arylacetonitriles in an alcoholic medium in the presence of excess alkali gives novel 2,1-benzisoxazoles. These findings indicate a high reactivity of nitroarenes activated by the azole ring due to their electron-deficient character. Moreover, it was found that annulation of the isoxazole ring occurred regioselectively in disubstituted nitroarenes. In the case of 1-(4-nitrophenyl)-1H-tetrazole, the tetrazole ring cleaved faster than the sH-adduct was formed. Georg Thieme Verlag Stuttgart.

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.

Studies on Selective Nucleophilic Substitution Reactions of + PF6- Complexes (M = Fe, Ru)

Reactions of + PF6- complexes (M = Fe, Ru) with phenoxide nucleophiles were found to proceed with excellent selectivity under mild conditions to give products of monosubstitution.Using aminophenoxides, a preference for O-arylation was observed, while amino alcohols such as prolinol react selectively on nitrogen.Methodology for sequential selective displacement of both chlorides by different nucleophiles is reported.