2597-56-0

Usage

Uses

Used in Organic Synthesis:
2-Methoxy-4-nitrobenzoic acid is used as a starting material in various organic syntheses for the creation of different chemical compounds.
Used in Pharmaceutical Industry:
2-Methoxy-4-nitrobenzoic acid is used as a starting material for the synthesis of:
1. 2-Methoxy-4-nitrobenzamide, a nitroamide derivative, which may have potential applications in the development of new pharmaceuticals.
2. 4-Amino-2-methoxybenzamide, an aminobenzamide derivative, which could be utilized in the creation of novel drug candidates.
3. N,2-Dimethoxy-N-methyl-4-nitrobenzamide, a Weinreb amide derivative, which might be employed in the synthesis of various bioactive molecules.
4. 1-(2-Methoxy-4-nitrophenyl)-5-methylhex-2-yn-1-one, a ynone derivative, which could be used in the development of new chemical entities.
5. 2,5-Constrained piperidine derivative, a potential CCR3 (Chemokine (C-C Motif) Receptor 3) antagonist, which may have applications in the treatment of various diseases related to the immune system.

InChI:InChI=1/C8H7NO5/c1-14-7-4-5(9(12)13)2-3-6(7)8(10)11/h2-4H,1H3,(H,10,11)

Upstream product

• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 108-24-7 acetic anhydride 
• 579-75-9 2-Methoxybenzoic acid 
• 136507-15-8 4-nitro-2-methoxybenzaldehyde 
• 619-19-2 2-hydroxy-4-nitrobenzoic acid 
• 77-78-1 dimethyl sulfate 
• 5428-54-6 2-methyl-5-nitrophenol 
• 74-88-4 methyl iodide 
• 555-03-3 3-nitroanisole 
• 191605-08-0 5-acetylamino-2-methoxy-benzoic acid 
• 106125-57-9 5-amino-2-methoxy-4-nitro-benzoic acid 
• 39106-79-1 methyl 2-methoxy-4-nitrobenzoate 
• 101080-01-7 2-chloromethyl-5-nitro-anisole 

Downstream Products

• 50712-57-7 (4-Amino-2-methoxyphenyl)essigsaeureethylester 
• 115919-39-6 2-methoxy-4,5-dinitrobenzoic acid 
• 617244-79-8 4-nitro-N-[2-(4-benzyl-piperazin-1-yl)-ethyl]-2-methoxy-benzamide 
• 617244-33-4 N-(N,N-dimethylaminoethylamine)-4-nitro-2-methoxybenzamide 
• 617244-91-4 4-amino-2-methoxy-N-(3-morpholin-4-yl-propyl)-benzamide 
• 619-19-2 2-hydroxy-4-nitrobenzoic acid 
• 136507-14-7 (2-methoxy-4-nitrophenyl)methanol 
• 251107-33-2 2-methoxy-3,4-dinitrobenzoic acid 
• 39106-79-1 methyl 2-methoxy-4-nitrobenzoate 
• 630125-56-3 (2-methoxy-4-nitro-phenyl)-piperidin-1-yl-methanone 
• 1232688-45-7 tert-butyl 2-methoxy-4-nitrobenzoate 
• 1314003-97-8 2-methoxy-4-nitrobenzoic acid benzyl ester 
• 1224963-02-3 2-methoxy-4-aminobenzoic acid benzyl ester 
• 1314003-74-1 C₁₆H₁₃NO₄ 

Relevant academic research and scientific papers

Synthesis of 2-Methoxy-4-(methylsulfanyl)benzoic Acid — An Intermediate Product in the Preparation of the Cardiotonic Drugs Sulmazole and Isomazole

Readily available 4-methyl-3-nitrobenzenesulfonic acid and 2-methyl-5-nitrophenol were used to develop two alternative approaches to the synthesis of 2-methoxy-4-(methylsulfanyl)benzoic acid in total yields of 17% and 37%, respectively. The synthesis starting from 2-methyl-5-nitrophenol is more process-oriented and can be used in the resynthesis of Sulmazole and Isomazole.

Metal-Free Aerobic Oxidation of Nitro-Substituted Alkylarenes to Carboxylic Acids or Benzyl Alcohols Promoted by NaOH

Efficient and selective aerobic oxidation of nitro-substituted alkylarenes to functional compounds is a fundamental process that remains a challenge. Here, we report a metal-free, efficient, and practical approach for the direct and selective aerobic oxidation of nitro-substituted alkylarenes to carboxylic acids or benzyl alcohols. This sustainable system uses O2 as clean oxidant in a cheap and green NaOH/EtOH mixture. The position and type of substituent critically affect the products. In addition, this sustainable protocol enabled gram-scale preparation of carboxylic acid and benzyl alcohol derivatives with high chemoselectivities. Finally, the reactions can be conducted in a pressure reactor, which can conserve oxygen and prevent solvent loss. The approach was conducive to environmental protection and potential industrial application.

Oligophenylenaminones as scaffolds for α-helix mimicry

The design and synthesis of small molecule α-helix mimetics has been a productive field over the past decade. These compounds have performed well in a variety of biological systems as functional disruptors of α-helix- mediated protein-protein interactions. In our studies we have continued to develop novel, more biologically compatible scaffolds, which are often easier to assemble and capable of mimicking longer and/or more diverse helices. To this end, we have constructed a new series of i, i+4, i+7 α-helix mimics based on the enaminone scaffold. These molecules represent a step forward in the pursuit of idealized monofacial α-helix mimetics.

Design and Synthesis of Novel Cyclooxygenase-1 Inhibitors as Analgesics: 5-Amino-2-ethoxy-N-(substituted-phenyl)benzamides

We previously found that N-(4-aminophenyl)-4-trifluoromethylbenzamide (TFAP), a COX-1 inhibitor, exhibits an analgesic effect without causing gastric damage. Unfortunately, TFAP causes reddish purple coloration of urine, and its analgesic effect is less potent than that of indomethacin. Herein we describe our study focusing on the development of 4- and 5-amino-2-alkoxy-N-phenylbenzamide scaffolds, designed on the basis of the structures of TFAP and parsalmide, another known COX-1 inhibitory analgesic agent. 5-Amino-2-ethoxy-N-(2- or 3-substituted phenyl)benzamide derivatives exhibited analgesic activity in a murine acetic acid induced writhing test. Among these compounds, 5-amino-2-ethoxy-N-(2-methoxyphenyl)benzamide (9v) possesses potent COX-1 inhibitory and analgesic activities, similar to those of indomethacin. In addition, 5-amino-2-ethoxy-N-(3-trifluoromethylphenyl)benzamide (9g) showed a more potent analgesic effect than indomethacin or 9v without causing apparent gastric damage or coloration of urine, although its COX-1 inhibitory activity was weaker than that of indomethacin or 9v. Thus, 9g and 9v appear to be promising candidates for analgesic agents and are attractive lead compounds for further development of COX-1 inhibitors.

PRODRUGS OF OPIOIDS AND USES THEREOF

The present invention concerns prodrugs of opioid analgesics and pharmaceutical compositions containing such prodrugs. Methods for providing more consistent pain relief by increasing the bioavailability of the opioid analgesic with the aforementioned prodrugs are provided. The invention also provides for decreasing the adverse GI side effects of opioid analgesics.

Effect of aldehyde and methoxy substituents on nucleophilic aromatic substitution by [18F]fluoride

For a series of benzaldehydes only with a leaving group or with both a leaving group and a single methoxy substituent 18F-fluorination via nucleophilic aromatic substitution (SNAr) was studied in DMF and Me2SO. In general, the radiochemical yields were clearly higher in DMF than in Me2SO. In the fluorodehalogenation reaction (leaving group: halogen = Br, Cl), extremely low radiochemical yields were observed in Me2SO (2SO (within 3 min reaction time, 90% of the precursor was consumed; radiochemical yield = 1.0 ± 0.5%); however, in DMF oxidation was always kept at a low level during the entire reaction (13C-NMR ppm values of the aromatic carbon atom bearing the leaving group.