870997-57-2

Usage

Uses

Used in Food and Beverage Industry:
Methyl 2-amino-3-methylbenzoate is used as a flavoring agent for its distinctive grape-like aroma, enhancing the taste of grape and orange-flavored products.
Used in Fragrance Industry:
In the fragrance industry, methyl 2-amino-3-methylbenzoate is used as a component in perfumes, contributing to the creation of complex and appealing scents.
Used as an Insect Repellent:
Methyl 2-amino-3-methylbenzoate is utilized as an insect repellent, taking advantage of its natural properties to deter insects and provide protection against bites.
Used in Pharmaceutical Research:
Methyl 2-amino-3-methylbenzoate is used as a subject of interest in pharmaceutical research due to its potential as an anti-inflammatory and analgesic agent, offering new possibilities for the development of medications.
However, it is crucial to handle Methyl 2-amino-3-methylbenzoate with care, as it can cause eye and skin irritation and is harmful if swallowed or inhaled in large amounts.

InChI:InChI=1/C9H12N2O/c1-6-4-3-5-7(8(6)10)9(12)11-2/h3-5H,10H2,1-2H3,(H,11,12)

Upstream product

• 1012861-61-8 3-methyl-2-sulfinylaminobenzoyl chloride 
• 74-89-5 methylamine 
• 66176-17-8 6-methylisatoic anhydride 
• 4389-45-1 3-methylantranilic acid 
• 99-04-7 m-Toluic acid 
• 773837-37-9 sodium cyanide 
• 890707-30-9 2-amino-5-bromo-N,3-dimethylbenzamide 
• 151-50-8 potassium cyanide 
• 143-33-9 sodium cyanide 
• 5437-38-7 3-methyl-2-nitrobenzoic acid 
• 600126-70-3 N-3-dimethyl-2-nitrobenzamide 

Downstream Products

• 1012861-65-2 N-(2-methyl-6-methylcarbamoyl-phenyl)-oxalamic acid ethyl ester 
• 870997-58-3 2-(4-methoxyphenyl)-3,8-dimethylquinazolin-4(3H)-one 
• 1257069-92-3 C₂₁H₂₀ClN₅O₄ 
• 1612771-82-0 3,8-dimethyl-2-phenyl-2,3-dihydroquinazolin-4(1H)-one 
• 1612771-88-6 2-(3-methoxyphenyl)-3,8-dimethyl-1,2,3,4-tetrahydroquinazolin-4-one 
• 500008-45-7 rynaxypyr 
• 1022969-81-8 2-(2,5-dichloro-pyrimidin-4-ylamino)-3,N-dimethyl-benzamide 
• 1022971-96-5 2-[5-chloro-2-(5,5-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-ylamino)-pyrimidin-4-ylamino]-3,N-dimethyl-benzamide 
• 890707-30-9 2-amino-5-bromo-N,3-dimethylbenzamide 
• 890707-28-5 2-amino-3-methyl-5-chlorobenzoyl-N-methylamine 

Relevant academic research and scientific papers

PROCESS FOR THE PREPARATION OF CHLORANTRANILIPROLE

The present invention relates to two novel, efficient and one-pot methods for synthesizing chlorantraniliprole. In the first scheme, Chlorantraniliprole is prepared by a novel telescopic process starting from 3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid a key raw material-A (Key RM-A). In the second scheme, starting from Key RM-A, the process steps use of a novel variant of anthranilic acid (Methyl 2-amino-5-chloro-3-methylbenzoate), to get Chlorantraniliprole. Furthermore, the present invention also relates to the synthesis of key starting material for the synthesizing chlorantraniliprole in-situ. All the in-situ steps of the disclosed synthesis methods obtain good yield, without using any expensive reagent or base or harsh reaction conditions, which makes the process simple, environment friendly and more cost effective. With this process the production cost of chlorantraniliprole and its intermediates is substantially reduced; fewer by-products are formed during its synthesis and since it's a one-pot reaction, isolation and purification are easy to achieve.

Improved synthesis process of 2-amino-5-chloro-N, 3-dimethylbenzamide

The invention discloses an improved synthesis process of 2-amino-5-chloro-N, 3-dimethylbenzamide, which comprises the following steps: preparing an instrument and a reagent for synthesizing 2-amino-5-chloro-N, 3-dimethylbenzamide, synthesizing 12-amino-3-methylbenzoic acid in a three-neck flask, adding ferric trichloride hexahydrate and activated carbon, stirring, heating, reacting, cooling, filtering, adding 2328-methyl-2H-3, 1-benzoxazine-2, 4(1H)-dione (MAD, 3) into a three-necked flask, adding 2-amino-3-methylbenzoic acid (MAA), pyridine and nitrile, heating under stirring until the reaction is completed, adding the reaction solution obtained in the second step into the three-neck flask, heating under stirring, then dropwise adding a mixed solution of sulfonyl chloride and acetonitrile, carrying out heat preservation reaction, then cooling to room temperature, directly filtering the reaction solution, and distilling the filtered filtrate to obtain 3-dimethylbenzamide. According tothe method for preparing the 2-amino-5-chloro-N, 3-dimethylbenzamide, the working procedure is simple and perfect in the process of preparing the 2-amino-5-chloro-N, 3-dimethylbenzamide, the preparation time can be well shortened, and the product quality is guaranteed.

Method for synthesizing chlorantraniliprole

A solvent containing 2 - amino -3 - methylbenzoic acid is stirred, N - methyl -3 - methyl -2 - amino - benzamide is dissolved in alkali liquor in a stirring reaction process, and reacted with NCS to obtain N - methyl -3 - methyl -2 - amino -5 - chloro - benzamide. The reaction of the bromination reaction, the oxidation reaction and the condensation reaction is carried out by cooperation of a catalyst so as to obtain chlorantraniliprole. By optimizing the preparation steps of chlorantraniliprole, the whole process is relatively simple in process steps, the post-treatment is simple, intermediate products can be obtained directly after the single step is finished, high environmental control requirements are not needed in the whole synthesis step, and industrialization can be conveniently realized.

Insecticide containing chlorantraniliprole (by machine translation)

Of the insecticide, is prepared, by compounding chlorantraniliprole, methoxyfenozide and indoxacarb as an active ingredient, wherein the insecticide synergistic effect is remarkably: by mass ratio of chlorantraniliprole: methoxyfenozide=2:1:1; indoxacarb, and the cost is low. (by machine translation)

A synthesis method of chlorine insect benzamide (by machine translation)

The present invention discloses one kind of chlorine insect benzamide synthesis method, relates to the field of organic synthesis. The invention two key intermediate 1 - (3 - chloro - 2 - pyridyl) - 3 - bromo - 1 H - 5 - pyrazole carboxylic acid with N - methyl - 3 - methyl - 2 - amino - 5 - chloro - benzamide synthesis method to re-design and improvement. Finally through the amidation reaction synthesize a final product chlorine insect benzamide. The synthesizing method of the invention for the intermediate 1 - (3 - chloro - 2 - pyridyl) - 3 - bromo - 1 H - 5 - pyrazole carboxylic acid synthesis provides a path; in the synthesis method steps of mild reaction conditions, and the steps can get better yield, overcomes the harsh reaction conditions in the prior art, the key steps to the problem of low yield, greatly reduces the production cost of the chlorine insect benzamide; in this synthetic method, the various steps in the few by-products, easy separation and purification, to further facilitate the industrial production. (by machine translation)

Diversification of quinazolinones by Pd-catalyzed C(sp3)-acetoxylation

The quinazolinone ring has been exploited as a directing group for C(sp3)-H functionalization for the first time. The proximal C-γ(sp3)-H bonds have been oxidized by palladium-catalyzed acetoxylation reaction. Various functional grou

Synthesis and insecticidal activities of 2,3-dihydroquinazolin-4(1H)-one derivatives targeting calcium channel

A series of compounds containing dihydroquinazolinone moiety was designed and synthesized. Amine bridge part was changed in comparison with known anthranilic diamides insecticides. Their insecticidal activities against oriental armyworm (Mythimna separata) indicated that most of the compounds showed moderate to high activities at the tested concentrations. In particular, compounds 5a and 5k showed 80% larvicidal activities against oriental armyworm at the concentration of 5 mg/L. The present study also explored the possible effects of target compounds on the high voltage-gated calcium channel and the calcium channels in the endoplasmic reticulum in the central neurons isolated from the third instar larvae of Spodoptera exigua using whole-cell patch clamp and calcium imaging technique. The results showed that compound 5a activated the high voltage-gated calcium channel in the central neurons of S. exigua weakly. The peak currents only increased by 6% of the initial value at the end of the 10-min recording after treated with 0.22 μM 5a, while chlorantraniliprole has an opposite effect. The effects of 5a on the intracellular calcium ion concentration ([Ca2+]i) in neurons were well investigated. The experimental results indicated that these novel compounds have different mechanism compared with chlorantraniliprole.

Fused bicyclic derivatives of 2,4-diaminopyrimidine as c-Met inhibitors

The HGF-c-Met signaling axis is an important paracrine mediator of epithelial-mesenchymal cell interactions involving the regulation of multiple cellular activities including cell motility, mitogenesis, morphogenesis, and angiogenesis. Dysregulation of c-Met signaling (e.g., overexpression or increased activation) is associated with the development of a wide range of tumor types; thus, inhibiting the HGF-c-Met pathway is predicted to lead to anti-tumor effects in many cancers. Elaboration of a 2-arylaminopyrimidine scaffold led to a series of potent c-Met inhibitors bearing a C4-2-amino-N-methylbenzamide group. Specifically, a series of C2-benzazepinone analogs demonstrated potent inhibition of c-Met in enzymatic and cellular assays. Kinase selectivity could be tuned by varying the nature of the alkyl group on the benzazepinone nitrogen.

2,4-Diaminopyrimidine inhibitors of c-Met kinase bearing benzoxazepine anilines

Elaboration of the SAR around a series of 2,4-diaminopyrimidines led to a number of c-Met inhibitors in which kinase selectivity was modulated by substituents appended on the C4-aminobenzamide ring and the nature of the C2-aminoaryl ring. Further lead opt

Synthesis and insecticidal activities of novel anthranilic diamides containing modified N-pyridylpyrazoles

In order to look for novel insecticides targeting the ryanodine receptor, four new series of anthranilic diamides containing modified N-pyridylpyrazoles were designed and synthesized. All of the compounds were characterized and confirmed by 1H NMR, 13C NMR, and HRMS. The single crystal structure of 10c was determined by X-ray diffraction. 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, while compound 19 showed comparable higher activity at the concentration of 0.125 mg/L. The preliminary structure-activity relationship (SAR) was discussed.