Category: 18595-12-5

Adding a certain compound to certain chemical reactions, such as: 18595-12-5, name is Methyl 5-amino-2-methylbenzoate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 18595-12-5, HPLC of Formula: C9H11NO2

Combine methyl 2-methyl-5-aminobenzoate (4.5 g, 27.2 mmol) and triethyl orthoformate (16.2 g, 109 mmol) in glacial acetic acid (25 mL). After 12 hours, add portionwise sodium azide (7.08 g, 109 mmol). Heat to 70 C. After 2 hours, cool the reaction mixture to ambient temperature, dilute with water (250 mL). Collect the solid by filtration, rinse with water, and dry to give methyl 2-methyl-5-(1H-tetrazol-1-yl)benzoate: Rf=0.13 (silica gel, ethyl acetate/hexane 1/4).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Maynard, George D.; Le, Tieu-Binh; US2001/34343; (2001); A1;; ; Patent; Aventis Pharmaceuticals Inc.; US6194406; (2001); B1;,
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Ester – an overview | ScienceDirect Topics

Synthetic Route of 18595-12-5,Some common heterocyclic compound, 18595-12-5, name is Methyl 5-amino-2-methylbenzoate, molecular formula is C9H11NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a 0 C. solution of methyl 5-amino-2-methylbenzoate (6.25 g, 37.8 mmol) in H2SO4 (10 mL) and H2O (160 mL) was added NaNO2 (aq., 3.78 N, 10 mL). The resulting mixture was stirred at 0 C. for 10 minutes. After 10 minutes, the mixture was added to a refluxing solution of CuSO4 (1 N, 100 mL) and refluxed for 1 hour. The mixture was cooled to room temperature and extracted with CH2Cl2 (2*200 mL). The organic layers were washed with H2O (50 mL) and brine (50 mL), dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/EtOAc=5:1) to give methyl 5-hydroxy-2-methylbenzoate (134a, 4.2 g, 67%) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 5-amino-2-methylbenzoate, its application will become more common.

Reference:
Patent; PFIZER INC.; EDWARDS, Martin Paul; KUMPF, Robert Arnold; KUNG, Pei-Pei; MCAPLINE, Indrawan James; NINKOVIC, Sacha; RUI, Eugene Yuanjin; SUTTON, Scott Channing; TATLOCK, John Howard; WYTHES, Martin James; Zehnder, Luke Raymond; US2014/179667; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 18595-12-5, name is Methyl 5-amino-2-methylbenzoate, molecular formula is C9H11NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. COA of Formula: C9H11NO2

4.6 g (28 mmol) of methyl 3-amino-6-methylbenzoate are dissolved in 50 ml of THF and 50 ml of 1M sulphuric acid and then the reaction medium is cooled to 0 C. A solution of sodium nitrite (2.3 g, 33.6 mmol) in 10 ml of water is then added dropwise and then the medium is stirred for 20 minutes. 15 ml of pure sulphuric acid are then added and the reaction medium is heated under reflux for 2 hours, poured into 500 ml of water and extracted with ethyl ether. The organic phases are dried, concentrated under reduced pressure and the residue obtained is dissolved in 100 ml of methanol. 3 ml of sulphuric acid are added and the reaction medium is heated under reflux for 14 hours, cooled, treated with water and ethyl ether. After extraction with ethyl ether, the organic phases are combined, dried over magnesium sulphate and concentrated under reduced pressure. After purification on a silica column (ethyl acetate 30-heptane 70), a brown oil is obtained (m=1.2 g; Y=25%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 18595-12-5, its application will become more common.

Reference:
Patent; Galderma Research & Development S.N.C.; US6689922; (2004); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 18595-12-5, name is Methyl 5-amino-2-methylbenzoate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 18595-12-5, Recommanded Product: 18595-12-5

Combine methyl 2-methyl-5-aminobenzoate (4.5 g, 27.2 mmol) and triethyl orthoformate (16.2 g, 109 mmol) in glacial acetic acid (25 mL). After 12 hours, add portionwise sodium azide (7.08 g, 109 mmol). Heat to 70 C. After 2 hours, cool the reaction mixture to ambient temperature, dilute with water (250 mL). Collect the solid by filtration, rinse with water, and dry to give methyl 2-methyl-5-(1H-tetrazol-1-yl)benzoate: Rf=0.13 (silica gel, ethyl acetate/hexane 1/4).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Maynard, George D.; Le, Tieu-Binh; US2001/34343; (2001); A1;; ; Patent; Aventis Pharmaceuticals Inc.; US6194406; (2001); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 18595-12-5, These common heterocyclic compound, 18595-12-5, name is Methyl 5-amino-2-methylbenzoate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step 1 Preparation of 1-[1-(2-toluoylmethyl)-2-oxo-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-methoxycarbonyl-4-methylphenyl)urea Methyl 5-amino-2-methylbenzoate (223 mg) was dissolved in tetrahydrofuran (30 ml), under ice-cooling triphosgene (135 mg) was added, triethylamine (116 mul) was added thereto five times every 3 minutes, the mixture was stirred for 10 minutes at same temperature. Subsequently, a solution of 1-(2-toluoylmethyl)-2-oxo-3-amino-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (500 mg) in tetrahydrofuran (20 ml) was added dropwise, stirred for 30 minutes at same temperature, and then stirred for 3 hours at room temperature. The reaction mixture was concentrated under reduced pressure, water (50 ml) was added, and extracted with methylene chloride. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography(chloroform:ethyl acetate=10:1), to thereby obtain 271 mg of the titled compound. 1H-NMR(CDCl3) delta: 1.04(9H, s), 2.39(3H, s), 2.50(3H, s), 2.52(3H, s), 3.83(3H, s), 3.96(1H, dd), 4.34(1H, t), 4.43(1H, d), 4.79-4.89(1H, m), 5.50(1H, d), 6.01(1H, d), 6.89(1H, brs), 7.03(1H, s), 7.03-7.35(6H, m), 7.43(1H, t), 7.69(1H, d), 7.88(1H, d)

Statistics shows that Methyl 5-amino-2-methylbenzoate is playing an increasingly important role. we look forward to future research findings about 18595-12-5.

Reference:
Patent; Zeria Pharmaceutical Co., Ltd.; US6239131; (2001); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 18595-12-5, A common heterocyclic compound, 18595-12-5, name is Methyl 5-amino-2-methylbenzoate, molecular formula is C9H11NO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 82; Preparation of inhibitor methyl 5-(5-(4-((4~methyipiperazin-1-yl)methyl)- benzamido)-2-methylbenzamido- 1 H-pyrro/o/2, 3-b]pyridine-2-carboxylate (ND0117); Step 1 : Preparation of methyl5-(4-(chloromethyl)benzamido)-2-methylbenzoate; A reactor is charged with 1g (6.06 mmol) of methyl 3-amino-6-methylbenzoate and 1.2g (119 mmol) of triethylamine in 25 ml of dichloromethane. 1.145g (6.05 mmol) of 4-chioromethylbenzoyle chloride is then added and the mixture is stirred at room temperature for 2 hours. The reacting medium is then washed with 10 ml of a saturated NaHCO3 solution, 10 ml of water and 10 ml of a saturated NaCI solution. The organic phase is dried, evaporated and the obtained residue is triturated in ethylic ether and then in pentane to give a white solid (1.2 g, 66%).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; NOVA DECISION; AZASYNTH; YASRI, Abdelaziz; CHEVE, Gwenael; BORIES, Cedric; DELON, Louis; WO2010/92489; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 18595-12-5, name is Methyl 5-amino-2-methylbenzoate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 18595-12-5, Safety of Methyl 5-amino-2-methylbenzoate

General procedure: To a solution of compound 11a (154 mg, 1.0 mmol) in anhydrous CH2Cl2 (10 mL) was added 3,5-dichlorobenzoyl chloride (209 mg, 1.0 mmol) and pyridine (241 mL 3.0 mmol) under ice bath. After stirring at room temperature for about 8 h, the solvent was removed in vacuum. The resulting residue was dissolved in NaOH (1 M) water solution (3 mL) and CH3OH (3 mL) and stirred for another 2 h. Then the solvent was removed under vacuum, and the residue was acidied to pH 2 or below with HCl (1 M) water solution. The solution was extracted with ethyl acetate twice and the combined organics were dried over anhydrous sodium sulfate and concentrated in vacuum. The resulting residue was puried by silica gel chromatography to give the desired compound as a white solid (234 mg, yield 85.0%)

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Gao, Ding-Ding; Dou, Hui-Xia; Su, Hai-Xia; Zhang, Ming-Ming; Wang, Ting; Liu, Qiu-Feng; Cai, Hai-Yan; Ding, Hai-Peng; Yang, Zhuo; Zhu, Wei-Liang; Xu, Ye-Chun; Wang, He-Yao; Li, Ying-Xia; European Journal of Medicinal Chemistry; vol. 154; (2018); p. 44 – 59;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 18595-12-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 18595-12-5 name is Methyl 5-amino-2-methylbenzoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a stirred solution of THF (5 mL) containing compound 3 (350 mg, 1.03 mmol) were added sequentially, HOBT (224 mg,1.6 mmol), EDC.HCl (306 mg, 1.6 mmol), TEA (0.28 mL, 2.0 mmol) and methyl 5-amino-2-methylbenzoate (3a) (198 mg, 1.2 mmol). The resulting mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with dichloromethane (10 mL) followed by water (15 mL), the organic layer was separated, washed with water (2 ¡Á 15 mL) followed by brine solution to obtain the crude compound 4. The crude compound was purified by column chromatography using 60-120 silica gel and eluted with 30 % EtOAc/hexane to afford compound 4. Pale white solid; Yield: 280 mg, 66 %; m.p.: 160-162 C; IR (neat, numax): 3431, 2925, 2858, 1620,1442, 1255, 1219, 1170, 1079, 954; 1H NMR: (CDCl3, 400 MHz): delta 7.96 (br.s, 1H-NH), 7.66 (d, J = 6.4 Hz, 1H), 7.46 (t, J = 7.2 Hz, 1H), 7.34 (d, J = 7.6Hz, 1H), 7.22 – 7.33 (d, 4 H),4.68 (br.p, 1H), 3.90 (s, 3H), 3.8(t,1H),3.06 (br.t, 2H) 2.55 (s,3 H)2.47(q, 1H) 1.87-2.03 (m, 4 H). ESI MS: m/z (rel. abund.%): 465.37 (M+,100).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 5-amino-2-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Article; Reddy; Prasad; Venkataramana; Asian Journal of Chemistry; vol. 28; 1; (2016); p. 138 – 142;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 18595-12-5, name is Methyl 5-amino-2-methylbenzoate, A new synthetic method of this compound is introduced below., Safety of Methyl 5-amino-2-methylbenzoate

2-Methyl-5-cyanobenzoic Acid Methyl Ester (42). CuCN (228 mg, 2.5 mmol) was suspended in distilled water (2 mL). NaCN (353 mg, 7.2 mmol) was added with vigorous stirring, and the internal temperature was kept below 40 C. until all the CuCN went into solution. A suspension of amine 41 (350 mg, 2.1 mmol) in water (4 mL) and conc. HCl (0.7 mL) was stirred and cooled in an ice bath. When the temperature reach 5 C., a solution of NaNO2 (190 mg, 2.8 mmol) in water (0.6 mL) was added dropwise at 5 C. When all the NaNO2 was added, the solution was added dropwise the NaCN/CuCN solution at 0 C. A few drops of methanol were added to keep the foaming under control. Stirring was continued for 3 h at 23 C. The suspension was extracted with EtOAc, and the organic layers were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give compound 42 (115 mg, 31%) as a colorless oil, Rf=0.63 (hexane:EtOAc=1:1). 1H NMR (400 MHz, CDCl3): delta 8.08 (d, 1H, J=1.7 Hz), 7.56 (dd, 1H, J=1.7 and 7.9 Hz), 7.28 (d, 1H, J=7.9 Hz), 3.83 (s, 3H), 2.56 (s, 3H). 13CNMR (100 MHz, CDCl3): delta 165.7, 145.5, 134.4, 134.1, 132.4, 130.3, 117.8, 109.7, 52.1, 21.8.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; PURDUE RESEARCH FOUNDATION; US2011/269834; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 18595-12-5, name is Methyl 5-amino-2-methylbenzoate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 18595-12-5, HPLC of Formula: C9H11NO2

Methyl 5-amino-2-methylbenzoate (1.0 eq, 3.75 g) was dissolved in acetic acid (70 ml). N-Iodosuccinimide (1.0 eq, 5.27 g) was added portionwise over 60 minutes. The mixture was stirred at room temperature for 30 minutes. Acetic acid was evaporated. The residue was diluted with ethyl acetate (80 ml) and neutralized with saturated sodium carbonate (80 ml). The organic layer was washed with 1M sodium thiosulfate (2¡Á40 ml), then water (2¡Á40 ml) and brine (2¡Á40 ml). The material was purified by flash chromatography on silica gel (gradient 10% to 30% ethyl acetate in hexanes) to provide methyl 5-amino-4-iodo-2-methylbenzoate as a yellow-orange solid (3.19 g, 49% yield). GCMS>95% pure, m/z 291. 1H NMR (400 MHz, DMSO, d6) delta 2.30 (s, 3H), 3.78 (s, 3H), 5.27 (br s, 2H), 7.24 (s, 1H), 7.54 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 5-amino-2-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; CHUA, Peter C.; Haddach, Mustapha; Nagasawa, Johnny Y.; Pierre, Fabrice; Whitten, Jeffrey P.; US2009/239859; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics