66176-17-8

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Methyl-isatoic anhydride is used as a key intermediate for the synthesis of various pharmaceuticals due to its ability to form stable intermediates and its versatile reactivity, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Production:
In the agrochemical industry, 3-Methyl-isatoic anhydride serves as a building block in the creation of compounds used in crop protection and pest management, leveraging its reactivity to produce effective and stable agrochemical products.
Used in Organic Synthesis:
3-Methyl-isatoic anhydride is utilized as a crucial component in the synthesis of heterocyclic compounds, which are important in various chemical and pharmaceutical applications, highlighting its role in expanding the scope of organic chemistry.

InChI:InChI=1/C9H7NO3/c1-5-3-2-4-6-7(5)10-9(12)13-8(6)11/h2-4H,1H3,(H,10,12)

Upstream product

• 1127-59-9 7-methyl-1H-indole-2,3-dione 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 4389-45-1 3-methylantranilic acid 
• 4124-31-6 trichloroacetic acid anhydride 
• 503-38-8 trichloromethyl chloroformate 
• 5437-38-7 3-methyl-2-nitrobenzoic acid 
• 669713-59-1 C₁₃H₁₇NO₄ 
• 530-62-1 1,1'-carbonyldiimidazole 
• 75-44-5 phosgene 

Downstream Products

• 33373-90-9 2-amino-3-methyl-N-thiazol-2-yl-benzamide 
• 22223-49-0 methyl 2-amino-3-methylbenzoate 
• 870997-57-2 N-methyl-3-methyl-2-aminobenzamide 
• 1233882-11-5 3-bromo-N-(2-methyl-6-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide 
• 1885-32-1 2-amino-3-methylbenzamide 
• 890707-28-5 2-amino-3-methyl-5-chlorobenzoyl-N-methylamine 
• 1064445-77-7 2-[2-(2-chloro-phenyl)-5-trifluoromethyl-2H-pyrazol-3-yl]-8-methyl-benzo[d][1,3]oxazin-4-one 
• 926197-46-8 2-amino-N-cyclopropyl-3-methylbenzamide 
• 631911-96-1 (2-bromo-3-methyl-5-nitro-phenyl)-carbamic acid tert-butyl ester 
• 631911-95-0 2-bromo-3-methyl-5-nitrobenzoic acid 
• 631911-94-9 2-amino-3-methyl-5-nitro-benzoic acid methyl ester 

Relevant academic research and scientific papers

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.

Aryl or heteroaryl methoxylation reaction method

The invention discloses an aryl or heteroaryl methoxylation reaction method. The method comprises the following steps: preparing a substrate. The coupling agent, ligand, solvent, catalyst and base are mixed homogeneously in an inert gas to give the aryl or heteroaryl methoxy compounds. Compared with a methoxylation reaction method in the prior art, the method has the advantages that the reaction system conditions are mild, the usage amount of the catalyst and the ligand is low to 5% of the amount of the substrate material, and the catalytic efficiency is improved. The method has better compatibility to different substrate expansion and discovery of aryl halides or heteroaryl halides with different functional groups. The yield of aryl or heteroaryl methoxy compounds prepared by the method disclosed by the invention is 36% - 89%.

Synthesis and structure-insecticidal activity relationship of novel phenylpyrazole carboxylic acid derivatives containing fluorine moiety

A series of novel phenylpyrazole carboxylic acid derivatives containing fluorine moiety, i.e., diamides 11, simple aryl-bearing amides 12 and acylthioureas 14 were successfully synthesized based on the key fluoro-containing phenylpyrazole acid intermediate. The new compounds were identified and confirmed by melting point, 1H NMR, 13C NMR and elemental analysis or HRMS. The bioassay results indicated that some of the compounds possessed excellent insecticidal activities towards oriental armyworm, diamondback moth and corn borer at low concentrations. For examples, compounds 11a, 11e?g and 14b exhibited remarkable larvicidal activities with LC50 values of 0.13 ? 0.39 mg/L and 0.0002 ? 0.0014 mg/L against oriental armyworm and diamondback moth, respectively, were comparable with those of the control chlorantraniliprole. Particularly, 11e were found superior to chlorantraniliprole in oriental armyworm tests (LC50: 0.23 mg/L vs. 0.26 mg/L); 11a, 11e, 11f and 14c in diamondback moth tests with LC50 values of 0.0002 mg/L, 0.0002 mg/L, 0.0008 mg/L and 0.0005 mg/L, respectively, were more effective than that of chlorantraniliprole. In addition, 12a also showed a promising insecticidal potential and development/optimization advantage. Compounds 11a, 11e–g, 12a, 14b and 14c could be considered as possible new leading structures for further study. The SAR investigation indicated that the compounds with fluorine motif (e.g., -F, -CF2H, -CF3) held apparently favorable insecticidal potentials, which provided useful guidance for further design/development of new phenylpyrazole-containing agrochemicals.

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)

Acyl thiourea and acyl urea derivatives containing trifluoromethylpyridine and application thereof

The invention discloses acyl thiourea and acyl urea derivatives containing trifluoromethylpyridine and an application thereof. A structure of the derivatives is shown in a general formula I. In the formula, definitions of R1, R2, R3, X and other groups are as shown in the description. The compound represented by the general formula I has excellent insecticidal activity, and can be used to preventand treat pests such as cotton bollworm, diamondback moth and brown planthopper, and can also be used to prevent and treat plant virus diseases such as TMV and CMV.

Synthesis and insecticidal activity study of novel anthranilic diamides analogs containing a diacylhydrazine bridge as effective Ca2+ modulators

Anthranilic diamides is a class of insecticides target at ryanodine receptors (RyRs). To discover potent insecticides targeting at RyRs, a series of novel anthranilic diamides with a diacylhydrazine bridge were designed and synthesized. Their insecticidal activities were evaluated and a preliminary structure-activity relationship (SAR) was summarized. In particular, compound 5g exhibited good lethality against oriental armyworm (Mythimna separata) at a concentration of 5?mg/L. The calcium imaging experimental results indicated that the compound 5g can serve as effective insect Ca2+ level modulators by disrupting the cellular calcium homeostasis in Mythimna separata (Walker) and Spodoptera exigua (Hübner), which probably activated the RyRs on the ER membrane.

QUINAZOLINE-PYRIDINE DERIVATIVES FOR THE TREATMENT OF CANCER-RELATED DISORDERS

Compounds that inhibit at least one of the A2A and A2B adenosine receptors, and compositions containing the compound and methods for synthesizing the compound, are described herein. Also described are the use of such compounds and compositions for the treatment of a diverse array of diseases, disorders, and conditions, including cancer- and immune-related disorders that are mediated, at least in part, by the adenosine A2A receptor and/or the adenosine A2B receptor.

Design, Synthesis, and Potency of Pyruvate Dehydrogenase Complex E1 Inhibitors against Cyanobacteria

Safe and effective algaecides are needed to control agriculturally and environmentally significant algal species. Four series (6, 10, 17, and 21) of 29 novel 4-aminopyrimidine derivatives were rationally designed and synthesized. A part of 10, 17, and 21 displayed potent inhibition of Escherichia coli pyruvate dehydrogenase complex E1 (E. coli PDHc-E1) (IC50 = 2.12-18.06 μM) and good inhibition of Synechocystis sp. PCC 6803 (EC50 = 0.7-7.1 μM) and Microcystis sp. FACH 905 (EC50 = 3.7-7.6 μM). The algaecidal activity of these compounds positively correlated with their inhibition of E. coli PDHc-E1. In particular, 21l and 10b exhibited potent algaecidal activity against PCC 6803 (EC50 = 0.7 and 0.8 μM, respectively), values that were 2-fold increased compared to that of copper sulfate (EC50 = 1.8 μM), and showed the best inhibition of cyanobacterium PDHc-E1 (IC50 = 5.10 and 6.06 μM, respectively). 17h and 21e, the best inhibitors of E. coli PDHc-E1, were studied by molecular docking, site-directed mutagenesis, and enzymatic assays. These results revealed that the improved inhibition of novel inhibitors compared with that of the lead compound I was due to the formation of a new hydrogen bond with Leu264 at the active site of E. coli PDHc-E1. The results proved the great potential to obtain effective algaecides via the rational design of PDHc-E1 inhibitors. [Figure Presented]

Isatoic anhydride and its process for synthesis of derivatives of

The invention discloses a synthesis method of isatoic anhydride and a derivative thereof, relating to the technical field of chemical synthesis. In the presence of catalysis of an organic selenium catalyst, isatin or a derivative thereof is oxidized by using hydrogen peroxide to prepare the isatoic anhydride and the derivative thereof. The synthesis method disclosed by the invention is simple and easily available in raw materials, low in cost, clean in oxidizing agent, free from a metal catalyst, and environmentally friendly, can be carried out in a neutral environment, and is small in corrosion to equipment.

Structure-activity relationship and properties optimization of a series of Quinazoline-2,4-diones as inhibitors of the canonical Wnt pathway

Wnt signaling pathway plays a critical role in numerous cellular processes, including tumor initiation, proliferation, invasion/infiltration, metastasis formation and resistance to chemotherapy. In a drug discovery project aimed at the identification of inhibitors of the canonical Wnt pathway, we selected a series of quinazoline 2,4-diones as starting point for the therapeutic treatment of glioblastoma multiforme. Despite of poor physico-chemical properties of hit compound 1, our medicinal chemistry effort allowed the discovery and characterization of lead compound 33 (SEN461), with improved ADME profile, good bioavailability and active in vitro and in vivo in glioblastoma, gastric and sarcoma tumors.