18595-17-0

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Amino-4-methylbenzoic acid methyl ester is utilized as an intermediate in the production of various pharmaceuticals, leveraging its chemical properties to facilitate the synthesis of medicinal compounds.
Used in Agrochemical Production:
In the agrochemical industry, 2-Amino-4-methylbenzoic acid methyl ester serves as a key component in the synthesis of pesticides and other agrochemical products, contributing to the development of effective solutions for crop protection.
Used in Dye and Pigment Manufacturing:
2-Amino-4-methylbenzoic acid methyl ester is employed as a starting material in the creation of dyes and pigments, where its chemical structure is manipulated to produce a range of colorants for various applications.
Used in Organic Compound Synthesis:
2-Amino-4-methylbenzoic acid methyl ester is also used as a building block in the synthesis of other organic compounds, highlighting its versatility in organic chemistry and its potential applications across different industries.
Used in Biological Research:
Due to its potential biological activities, including anti-inflammatory and anti-tumor properties, 2-Amino-4-methylbenzoic acid methyl ester is used in biological research to explore its therapeutic potential and mechanisms of action, which could lead to the development of new treatments for various diseases.

Upstream product

• 67-56-1 methanol 
• 2305-36-4 4-methylanthranilic acid 
• 1128-47-8 6-methylindoline-2,3-dione 
• 186581-53-3 diazomethane 
• 40314-06-5 5-methyl-1H-isoindole-1,3-(2H)-dione 
• 74-88-4 methyl iodide 

Downstream Products

• 140112-50-1 5-Methyl-2-((Z)-octadec-9-enoylamino)-benzoic acid methyl ester 
• 100038-82-2 2-(2-Carboxy-phenylamino)-4-methyl-benzoic acid methyl ester 
• 141541-77-7 (2-Isobutylamino-4-methyl-phenyl)-methanol 
• 128936-38-9 2-[(2-isobutylamino-4-methyl)benzylthio]imidazole 
• 128936-39-0 2-[(2-isobutylamino-4-methyl)benzylsulfinyl]imidazole 
• 4316-23-8 4-methylphthalic acid 
• 158579-76-1 methyl 4-methyl-2-(N-methylsulphonylamino)benzoate 
• 1042430-76-1 methyl 4-methyl-2-(1'-phenylpyrrolidin-2'-ylideneamino)benzoate 
• 929214-89-1 methyl 2-{[(5-chloropyridin-2-yl)carbonyl]amino}-4-methylbenzoate 
• 1227375-06-5 C₁₀H₉NO₃ 
• 1551021-81-8 C₁₂H₁₆N₂O₃*C₂HF₃O₂ 
• 1551021-86-3 C₂₅H₂₇ClN₂O₆ 

Relevant academic research and scientific papers

Chemoselectivity for Alkene Cleavage by Palladium-Catalyzed Intramolecular Diazo Group Transfer from Azide to Alkene

Alkenes can be cleaved by means of the (3+2) cycloaddition and subsequent cycloreversion of 1,3-dipoles, classically ozone (O3), but the azide (R?N3) variant is rare. Chemoselectivity for these azide to alkene diazo group transfers (DGT) is typically disfavored, thus limiting their synthetic utility. Herein, this work discloses a palladium-catalyzed intramolecular azide to alkene DGT, which grants chemoselectivity over competing aziridination. The data support a catalytic cycloreversion mechanism distinct from other known metal-catalyzed azide/alkene reactions: nitrenoid/metalloradical and (3+2) cycloadditions. Kinetics experiments reveal an unusual mechanistic profile in which the catalyst is not operative during the rate-controlling step, rather, it is active during the product-determining step. Catalytic DGT was used to synthesize N-heterocyclic quinazolinones, a medicinally relevant structural core. We also report on the competing aziridination and subsequent ring expansion to another N-heterocyclic core structure of interest, benzodiazepinones.

Discovery of β-Arrestin Biased, Orally Bioavailable, and CNS Penetrant Neurotensin Receptor 1 (NTR1) Allosteric Modulators

Neurotensin receptor 1 (NTR1) is a G protein coupled receptor that is widely expressed throughout the central nervous system where it acts as a neuromodulator. Neurotensin receptors have been implicated in a wide variety of CNS disorders, but despite extensive efforts to develop small molecule ligands there are few reports of such compounds. Herein we describe the optimization of a quinazoline based lead to give 18 (SBI-553), a potent and brain penetrant NTR1 allosteric modulator.

Iodine(III) Reagent-Mediated Intramolecular Amination of 2-Alkenylanilines to Prepare Indoles

A variety of 3-substituted and 2,3-disubstituted indoles were synthesized efficiently in good yields through the intramolecular amination of 2-alkenylanilines promoted by readily available iodine(III) reagents in a short reaction time. Mechanistic studies showed that the reaction pathway went through a nitrenium ion and that 3-acetoxy indoline was the key intermediate in the indole formation. The indole product was easily prepared on a gram scale and amination also proceeded smoothly using catalytic 3,5-dimethylphenyl iodine in the presence of mCPBA. Furthermore, the indolo[3,2-a]carbazole scaffold was prepared in good yield in six steps from commercial ortho-iodoaniline. (Figure presented.).

Constrained TRPV1 agonists synthesized via silver-mediated intramolecular azo-methine ylide cycloaddition of α-iminoamides

As part of an effort to identify agonists of TRPV1, a peripheral sensory nerve ion channel, high throughput screening of the NIH Small Molecule Repository (SMR) collection identified MLS002174161, a pentacyclic benzodiazepine. A synthesis effort was initi

Hofmann-type rearrangement of imides by in situ generation of imide-hypervalent iodines(III) from iodoarenes

The Hofmann-type rearrangement of aromatic and aliphatic imides using a hypervalent iodine(III) reagent generated in situ from PhI, m-CPBA, and TsOH·H2O proceeded in the presence of a base in alcohol to provide anthranilic acid derivatives and amino acid derivatives in high yields, respectively. This reaction proceeds through a tandem reaction via alcoholysis followed by a Hofmann rearrangement promoted by the formation of an imide-λ3-iodane intermediate.

DIHYDROOROTATE DEHYDROGENASE AS ANTIFUNGAL DRUG TARGET AND QUINAZOLINONE-BASED INHIBITORS THEREOF

A method of identifying an antifungal agent which targets a DHODH protein (alias PyrE, dihydroorotate dehydrogenase, EC: 1.3.99.11) of a fungus comprising contacting a candidate substance with a fungal DHODH protein and determining whether the candidate s

Synthesis of substituted indole from 2-aminobenzaldehyde through [1,2]-aryl shift

A mild, efficient, and simple method for the synthesis of 3-ethoxycarbonylindoles has been developed. Addition of ethyl diazoacetate (EDA) to 2-aminobenzaldehydes cleanly affords the indole core. As opposed to other common approaches for the synthesis of indole, this method displays both excellent functional group tolerance and perfect regiochemical control. This allowed the synthesis of a variety of useful indole building blocks from 2-aminobenzaldehydes derived from readily available anthranilic acids.

Parallel synthesis and spectroscopic analysis of a collection of heterocycles based on the diazabenz[e]aceanthrylene core structure

A practical strategy for the synthesis of diazabenz[e]aceanthrylene-based heterocycles is reported. The key step in this approach is a microwave-assisted condensation and cyclisation reaction between an anthranilic acid derivative and a 2′-carbomethoxy substituted N-aryl lactam. The scope of the reaction has been explored as a function of both the nature and position of substituents in both components and variations in lactam ring size. Interesting structural and spectroscopic variations observed across the compound collection are described and explored using NMR, X-ray crystallography and computational techniques.

LACTAM COMPOUNDS USEFUL AS PROTEIN KINASE INHIBITORS

The present invention provides novel compounds useful as inhibitors of protein kinases. The invention also provides pharmaceutical compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various diseases.

4-benzoyl isoxazoles derivatives and their use as herbicides

4-Benzoylisoxazole derivatives of the formula wherein R is H or an ester; R1is alkyl, haloalkyl or optionally substituted cycloalkyl; R2is halogen, optionally halogenated alkyl, alkenyl or alkynyl; alkyl substituted with one or more —OR5; —NO2, —CN, —CO2R5, —S(O)pR6, —O(CH2)mOR5, —COR5, —NR5R6, —N(R8)SOqR7, —CONR9R10or —OR51; or optionally substituted phenyl; R3is —S(O)qR7; X is —N(R8)—; n is 0, 1, 2, 3, or 4; R5, R51and R6are independently H; optionally halogenated alkyl, alkenyl or alkynyl; optionally substituted phenyl; or cycloalkyl; R7is optionally halogenated alkyl, alkenyl or alkynyl; cycloalkyl; optionally substituted phenyl; or optionally substituted amino; R8is H; optionally halogenated alkyl, alkenyl or alkynyl; cycloalkyl; optionally substituted phenyl; or alkoxy; m is 1, 2 or 3; p is 0, 1 or 2; q is 0 or 2; and their use as herbicides are described.