35472-56-1

Usage

Uses

Used in Flavor and Fragrance Industry:
Benzoic acid, 2-(methylamino)-, ethyl ester is used as a flavoring agent and fragrance ingredient for its fruity mandarin-type aroma. It provides a pleasant and refreshing scent to various products such as perfumes, colognes, soaps, and other personal care products.
Used in Food Industry:
Benzoic acid, 2-(methylamino)-, ethyl ester is used as a flavor enhancer in the food industry. It imparts a fruity and refreshing taste to various food products, contributing to a more enjoyable and appetizing experience for consumers.
Used in Cosmetics Industry:
Benzoic acid, 2-(methylamino)-, ethyl ester is used as a fragrance ingredient in cosmetics. It adds a pleasant and fruity scent to products such as lotions, creams, and shampoos, making them more appealing to users.
Used in Aromatherapy:
Benzoic acid, 2-(methylamino)-, ethyl ester can be used in aromatherapy for its fruity mandarin-type aroma. It may help create a relaxing and uplifting atmosphere, promoting a sense of well-being and reducing stress.

InChI:InChI=1/C10H13NO2/c1-3-13-10(12)8-6-4-5-7-9(8)11-2/h4-7,11H,3H2,1-2H3

Upstream product

• 33923-02-3 methyl N-methyl-N-carbethoxyanthranilate 
• 141814-27-9 2-(2-Methoxyethoxy)ethyl methyl carbonate 
• 87-25-2 2-ethoxycarbonylaniline 
• 4214-38-4 (diphenylmethylene)triphenylphosphorane 
• 10328-92-4 N-Methylisatoic anhydride 
• 76393-16-3 2-(ethoxycarbonyl)phenyl isocyanate 
• 50-00-0 formaldehyd 
• 610-16-2 N,N-dimethylanthranilic acid 
• 613-97-8 N-methyl-N-ethylaniline 
• 121-69-7 N,N-dimethyl-aniline 
• 118-48-9 isatoic anhydride 
• 122-51-0 orthoformic acid triethyl ester 
• 55426-74-9 dimethylaminobenzoic acid ethyl ester 
• 118-92-3 anthranilic acid 

Downstream Products

• 99105-33-6 N-chloroacetyl-N-methyl-anthranilic acid ethyl ester 
• 13082-16-1 1,2,3-Trimethoxy-N-methylacridon 
• 61352-48-5 ethyl N-(N-benzyl-2-pyrrolidinylcarbonyl)-N-methylanthranilate 
• 1345539-83-4 ethyl 2-(2,6-difluoro-N-methylbenzamido)benzoate 
• 1234481-21-0 XMD₁₂-70-2 
• 1234479-76-5 2-((2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)amino)-5,11-dimethyl-5,11-dihydro-6H-benzo[e]pyrimido[5,4-b][1,4]diazepin-6-one 
• 1234480-46-6 2-((2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)amino)-11-methyl-5,11-dihydro-6H-benzo[e]pyrimido[5,4-b][1,4]diazepin-6-one 
• 1234479-75-4 2-chloro-5,11-dimethyl-5,11-dihydro-6H-benzo[e]pyrimido[5,4-b][1,4]diazepin-6-one 
• 66427-86-9 2-chloro-11-methyl-5,11-dihydro-6H-benzo[e]pyrimido-[5,4-b][1,4]diazepin-6-one 
• 1234479-74-3 ethyl 2-((2-chloro-5-nitropyrimidin-4-yl)(methyl)amino)benzoate 
• 100717-76-8 3-butyl-4-hydroxy-1-methylquinolin-2(1H)-one 
• 57513-54-9 ethyl 4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate 
• 70744-03-5 3-amino-4-hydroxy-1-methyl-1H-quinolin-2-one 
• 719-54-0 10-methyl-9, 10-dihydro-9-acridinone 

Relevant academic research and scientific papers

Palladium/copper-catalyzed aerobic oxidative C-H carbonylation for the synthesis of o-aminobenzoates

The palladium/copper-catalyzed aerobic oxidative C-H carbonylation for the synthesis of o-aminobenzoates is described. Molecular oxygen is used as the terminal oxidant. This methodology proceeds with a wide range of N-substituted anilines and alcohols and gives straightforward access to valuable o-aminobenzoates.

Palladium-Catalyzed Multistep Tandem Carbonylation/N-Dealkylation/Carbonylation Reaction: Access to Isatoic Anhydrides

A novel and efficient synthesis of isatoic anhydride derivatives was developed via palladium-catalyzed multistep tandem carbonylation/N-dealkylation/carbonylation reaction with alkyl as the leaving group and tertiary anilines as nitrogen nucleophiles. This approach features good functional group compatibility and readily available starting materials. Furthermore, it provided a convenient approach for the synthesis of biologically and medicinally useful evodiamine.

A novel pathway for the thermolysis of N-nitrosoanthranilates using flash vacuum pyrolysis leading to 7-aminophthalides

Flash vacuum pyrolysis of methyl N-methyl-N-nitrosoanthranilate leads to elimination of nitric oxide and disproportionation of the formed N-radical to 7-(methylamino)phthalide and methyl N-methylanthranilate. This transformation was found to be a convenient, solvent-free method for the preparation of 7-(methylamino)phthalides. An alternative route through pyrolysis of N-benzyl-N-methyl anthranilates was also investigated. This journal is

One-Pot Total Synthesis of Evodiamine and Its Analogues through a Continuous Biscyclization Reaction

The one-pot total synthesis of evodiamine and its analogues is achieved using a three-component reaction. Through continuous biscyclization, various readily available substrates with good functional group tolerance were easily incorporated into biologically active quinazolinocarboline backbones. The use of triethoxymethane as a cosolvent was crucial for this quick and straightforward transformation.

Acetic Acid Accelerated Visible-Light Photoredox Catalyzed N-Demethylation of N,N-Dimethylaminophenyl Derivatives

N,N-Dimethylaminophenyl moiety is a common fragment in medicinal chemistry as several pharmaceuticals bearing this privileged motif are on the market and under clinical evaluation. Oxidative N-demethylation is generally regarded as the major metabolic pathway. However, pharmacokinetics, metabolites studies as well as the further structural modification are precluded by the impracticality of chemical synthesis. Here we report that acetic acid can significantly accelerate visible-light photoredox catalyzed N-demethylation of N,N-dimethylaminophenyl derivatives. This approach is easy for large scale reaction and even for potential industrial manufacture. (Figure presented.).

Chemoselective Schwartz Reagent Mediated Reduction of Isocyanates to Formamides

Addition of the in situ generated Schwartz reagent to widely available isocyanates constitutes a chemoselective, high-yielding, and versatile approach to the synthesis of variously functionalized formamides. Steric and electronic factors or the presence of sensitive functionalities (esters, nitro groups, nitriles, alkenes) do not compromise the potential of the method. Full preservation of the stereochemical information contained in the starting materials is observed. The use of formamides in the nucleophilic addition of organometallic reagents (Chida-Sato allylation, Charette-Huang addition to imidoyl triflate activated amides, Matteson homologation of boronic esters) is briefly investigated.

Optimisation of LRRK2 inhibitors and assessment of functional efficacy in cell-based models of neuroinflammation

LRRK2IN1 is a highly potent inhibitor of leucine-rich repeat kinase 2 (LRRK2, IC50 = 7.9 nM), an established target for treatment of Parkinson's disease. Two LRRK2IN1 analogues 1 and 2 were synthesised which retained LRRK2 inhibitory activity (1: IC50 = 72 nM; 2: IC50 = 51 nM), were predicted to have improved bioavailability and were efficacious in cell-based models of neuroinflammation. Analogue 1 inhibited IL-6 secretion from LPS-stimulated primary human microglia with EC50 = 4.26 μM. In order to further optimize the molecular properties of LRRK2IN1, a library of truncated analogues was designed based on docking studies. Despite lacking LRRK2 inhibitory activity, these compounds show antineuroinflammatory efficacy at micromolar concentration. The compounds developed were valuable tools in establishing a cell-based assay for assessing anti-neuroinflammatory efficacy of LRRK2 inhibitors. Herein, we present data that IL-1β stimulated U87 glioma cell line is a reliable model for neuroinflammation, as data obtained in this model were consistent with results obtained using primary human microglia and astrocytes.

Palladium-catalyzed oxidative carbonylation of aromatic C-H bonds of N -alkylanilines with CO and alcohols for the synthesis of o -aminobenzoates

A Pd(II)-catalyzed C-H monocarbonylation of N-alkylanilines for the synthesis of o-aminobenzoates has been developed. Various aliphatic alcohols and phenol were tolerated in the reaction to afford the corresponding o-aminobenzoates in good yields under mild balloon pressure of CO.

Palladium-catalyzed regioselective carbonylation of C-H bonds of N -alkyl anilines for synthesis of isatoic anhydrides

A Pd-catalyzed regioselective C-H bond carbonylation of N-alkyl anilines for the synthesis of isatoic anhydrides has been developed. The key Pd-catalyst intermediate has been isolated and characterized. This novel Pd-catalyzed carbonylation reaction tolerates a wide range of functional groups and is a reliable method for the rapid elaboration of readily available N-alkyl anilines into a variety of substituted isatoic anhydrides under mild conditions.

Anthranilic acid-based inhibitors of phosphodiesterase: Design, synthesis, and bioactive evaluation

Our previous studies identified two 2-benzoylaminobenzoate derivatives 1, which potently inhibited superoxide (O2-) generation induced by formyl-l-methionyl-l-leucyl-l-phenylalanine (FMLP) in human neutrophils. In an attempt to improve their activities, a series of anthranilic acid derivatives were synthesized and their anti-inflammatory effects and underlying mechanisms were investigated in human neutrophils. Of these, compounds 17, 18, 46, 49, and 50 showed the most potent inhibitory effect on FMLP-induced release of O2- in human neutrophils with IC50 values of 0.20, 0.16, 0.15, 0.06, and 0.29 μM, respectively. SAR analysis showed that the activities of most compounds were dependent on the ester chain length in the A ring. Conversely, a change in the linker between the A and B ring from amide to sulfonamide or N-methyl amide, as well as exchanges in the benzene rings (A or B rings) by isosteric replacements were unfavorable. Further studies indicated that inhibition of O2- production in human neutrophils by these anthranilic acids was associated with an elevation in cellular cAMP levels through the selective inhibition of phosphodiesterase 4. Compound 49 could be approved as a lead for the development of new drugs in the treatment of neutrophilic inflammatory diseases.