Category: 22223-49-0

Adding a certain compound to certain chemical reactions, such as: 22223-49-0, name is Methyl 2-amino-3-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 22223-49-0, SDS of cas: 22223-49-0

Step B Preparation of methyl 2-[[(2,2-dimethylhydrazino)carbonyl]amino]-3-methylbenzoate To a solution of the title compound of Step A (25.4 g, 154 mmol) in p-dioxane (500 mL) under a nitrogen atmosphere was added diphosgene (22.3 mL, 184 mmol), followed by triethylamine (25.6 mL, 184 mmol). A white precipitate formed, and the resulting mixture was heated to 60 C. overnight. The mixture was cooled to room temperature and filtered. The precipitate was washed with diethyl ether and the combined filtrates were concentrated under reduced pressure to afford an oil (30.97 g) which, without further characterization, was dissolved in toluene (400 mL). To this solution at 0 C. under a nitrogen atmosphere was added 1,1-dimethylhydrazine (12.3 mL, 162 mmol) and the resulting milky suspension was stirred at 0 C. for 30 min. The precipitate was collected by filtration and washed with hexanes to afford the title compound of Step B (25.57 g) as a beige solid. 1 H NMR (CDCl3): delta 9.22 (br s,1H), 7.75 (d,1H), 7.40 (d,1H), 7.14 (t,1H), 5.32 (br s,1H), 3.88 (s,3H), 2.66 (s,6H), 2.35 (s,3H).

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; E. I. du Pont de Nemours and Company; US5962436; (1999); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 22223-49-0, name is Methyl 2-amino-3-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 22223-49-0, Recommanded Product: Methyl 2-amino-3-methylbenzoate

A solution of methyl 2-amino-3-methylbenzoate (142.1 g, 0.843 mol, purity: 98% quantitative NMR) in 240 mL of H2O is gradually admixed at 30 C. with hydrogen bromide (48% of H2O, 149.2 g, 0.885 mol) added dropwise. The suspension obtained is admixed with hydrogen peroxide (30% in H2O, 105.1 g, 0.927 mol) added dropwise over 2 h, and the temperature is kept below 70 C. After 1 hour of subsequent stirring, NaHSO3 (39% in H2O, 33.7 g, 0.126 mol) is added a little at a time (peroxide test was negative). The suspension obtained is adjusted to pH7-8 with Na2CO3 (0.1 eq., 9.0 g, 0.084 mol), which is added a little at a time. Following filtration and drying in a vacuum drying cabinet, methyl 2-amino-5-bromo-3-methylbenzoate is isolated as a pale brown solid. Yield: 204.2 g, 97.7% of theory, purity: 98.5% quantitative NMR). 1H NMR (600 MHz, (d6-DMSO): delta=7.70 (d, 1H), 7.36 (pt, 1H), 6.63 (br s, 2H), 3.80 (s, 3H), 2.12 (s, 3H)).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-amino-3-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Volz, Frank; Himmler, Thomas; Mueller, Thomas Norbert; Lehmann, Sandra; Von Morgenstern, Sascha; Moradi, Wahed Ahmed; Pazenok, Sergii; Lui, Norbert; US2014/148611; (2014); A1;,
Ester – Wikipedia,
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Reference of 22223-49-0, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 22223-49-0 as follows.

A mixture of 2-amino-3-methylbenzoic acid (15.2 g, 0.10 mol), dimethylformamide (333 mL) and CsCO3 (49 g, 0.15 mol) was stirred at room temperature for about 40 minutes before drop wise addition of iodomethane (14.2 g, 6.2 mL, 0.10 mol) in dimethylformamide (“DMF”) (115 mL). The mixture was stirred . at room temperature overnight. The mixture was diluted with water (1 L), and extracted with diethyl ether. The aqueous phase was back extracted with diethyl ether. The combined organic extracts were washed with saturated aqueous NaCI, dried over MgSO4, filtered and concentrated. The resultant material was dried at room temperature/0.5 mmHg to afford methyl 2-amino-3-methylbenzoate (17 g, 100%).To a solution methyl 2-amino-3-methylbenzoate (16.5 g, 0.10 mol) in CHCI3 (286 mL) was added acetic anhydride (23.5 g, 21.7 mL, 0.23 mol) so as to maintain the internal temperature <40 0C. The mixture was stirred at room temperature for 1 hour before addition of potassium acetate (2.94 g, 30 mmol) and isoamyl nitrite (25.8 g, 30 mL, 0.22 mol). The resultant mixture was heated at reflux overnight. To this was then added methanol (94 mL) and 6 N HCI (94 mL) and the mixture was stirred overnight. The reaction mixture was concentrated to provide an orange solid which was subsequently triturated with ethyl acetate and the solids were isolated by vacuum filtration. The solids were dried at room temperature/0.5 mmHg to afford methyl 1 H-indazole-7-carboxylate (15.4 g, 88%). -A solution of methyl 1 H-indazole-7-carboxylate (14.96 g, 84.9 mmol) in methanol (180 ml_) was cooled to 0 0C before addition of 29% aqueous potassium hydroxide (36 ml_). The ice bath was removed and the reaction mixture was stirred at room temperature overnight. The pH was adjusted to 5.5 using concentrated HCI. The volatiles were removed by vacuum filtration and the resultant material was suspended in water (100 mL) and ethyl acetate (200 mL). The resultant precipitate was isolated by vacuum filtration and rinsed with ethyl acetate. The solids were dried at room temperature/0.5 mmHg to afford the title compound (7.54 g, 55%).

According to the analysis of related databases, 22223-49-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/65508; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 22223-49-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 22223-49-0, name is Methyl 2-amino-3-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1. To a solution of 17 (15.0 g, 90.8 mmol) in DMF (200 mL) was added NBS (16.2 g, 90.8 mmol) at 0C. After addition, the mixture was warmed to 15C and stirred for 14 hours. The reaction mixture was quenched by addition of water (200 mL) and then extracted with ethyl acetate (3 x 250 mL). The combined organic phase was washed with water (3 x 250 mL) and brine (2 x 200 mL), dried over anhydrous Na2S04, filtered and concentrated in vacuo to give 18 (21.0 g) as a gray solid which was used directly in the next transformation. 1H NMR (CDC13, 400MHz) delta 7.90-7.89 (d, 1H), 7.29-7.28 (d, 1H), 5.84 (s, 2H), 3.87 (s, 3H), 2.15 (s, 3H); LCMS (ESI): m/z 246.0 (M+H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 2-amino-3-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NUMERATE, INC.; RAIMUNDO, Brian; KOLTUN, Elena S.; GRIFFIN, John; STANGELAND, Eric; (50 pag.)WO2018/49328; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 22223-49-0, name is Methyl 2-amino-3-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 22223-49-0, SDS of cas: 22223-49-0

Step B Preparation of methyl 2-[[(2,2-dimethylhydrazino)carbonyl]amino]-3-methylbenzoate To a solution of the title compound of Step A (25.4 g, 154 mmol) in p-dioxane (500 mL) under a nitrogen atmosphere was added diphosgene (22.3 mL, 184 mmol), followed by triethylamine (25.6 mL, 184 mmol). A white precipitate formed, and the resulting mixture was heated to 60 C. overnight. The mixture was cooled to room temperature and filtered. The precipitate was washed with diethyl ether and the combined filtrates were concentrated under reduced pressure to afford an oil (30.97 g) which, without further characterization, was dissolved in toluene (400 mL). To this solution at 0 C. under a nitrogen atmosphere was added 1,1-dimethylhydrazine (12.3 mL, 162 mmol) and the resulting milky suspension was stirred at 0 C. for 30 min. The precipitate was collected by filtration and washed with hexanes to afford the title compound of Step B (25.57 g) as a beige solid. 1 H NMR (CDCl3): delta 9.22 (br s,1H), 7.75 (d,1H), 7.40 (d,1H), 7.14 (t,1H), 5.32 (br s,1H), 3.88 (s,3H), 2.66 (s,6H), 2.35 (s,3H).

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; E. I. du Pont de Nemours and Company; US5962436; (1999); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 22223-49-0, 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. 22223-49-0 name is Methyl 2-amino-3-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.

General procedure: CuCl (1.50 mg, 0.0150 mmol), DPEPhos (8.10 mg, 0.0150 mmol) and KOt-Bu (1.70 mg,0.0150 mmol) were added to a 8 mL vial charged with a magnetic bar. The vial was sealedwith a cap (phenolic open top cap with gray PTFE/silicone) and purged by N2 gas for 5 min.Toluene (0.8 mL) and methyl 2-aminobenzoate (1a) (46.6 L, 0.360 mmol) were added to themixture, which was allowed for 10 min. And then a solution of phenyl vinyl sulfone (2) (50.5mg, 0.300 mmol) in toluene (0.7 mL) was added to the reaction solution. After stirring atroom temperature for 5 h, THF (5 mL) was added and the reaction was allowed to cool to 0C (ice bath). After addition of KOt-Bu (101 mg, 0.900 mmol), the resulting solution wasallowed to stir for further 1 h at 0 C. After that time, the reaction was quenched with asaturated aqueous solution of NH4Cl (1 mL) and NaHCO3 (2 mL) and washed with EtOAc (7x 3 mL). The organic layers were combined, dried over MgSO4, filtered, and concentrated invacuo. The crude product was purified by silica gel column chromatography (CH2Cl2/EtOAc,8:1) to afford the desired product 4a (76.8 mg, 0.267 mmol, 89% yield) as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-amino-3-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Article; Kang, Seongil; Yoon, Hongju; Lee, Yunmi; Chemistry Letters; vol. 45; 12; (2016); p. 1356 – 1358;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 22223-49-0 as follows. HPLC of Formula: C9H11NO2

The mixture of pyridine-4-carboxylic acid (1.1199g; 9.0967mmol) dissolved in thionyl chloride (15mL; 206.7748mmol) were mixed and refluxed for 1-3h. Then the excess of thionyl chloride was distilled under vacuum and the aromatic amine methyl ester Ea (1.500g; 9.0816mmol) dissolved in CHCl3 (20mL; 249.6231mmol) was added. The mixture was heated and stirred under reflux for 3-6h. The amide (L2: yield ca. 50%; 1.2212g; 3.5627mmol) was precipitated as yellow crystals after washing the dark yellow oil with diethyl ether and recrystallization with the mixture of acetone and methanol (m.p. 180C). Anal. Calc. for (C15H15N2O3)Cl(H2O)2: C, 52.56; H, 5.59; N, 8.17. Found: C, 52.39; H, 6.30; N, 8.16. FT-IR (KBr): 3435cm-1 nu(O-H), 3218cm-1 nu(N-H), 3056, 2924, 2852cm-1 nu(C-H), 1730 and 1640cm-1 nu(C=O), 1603-1441cm-1 nu(ringC=C), 1317-1088cm-1 nu(C-O) and nu(C-N) overlapped, 803/750cm-1 delta(ringC=C)oop. 1H NMR (403MHz, d-DMSO, ppm) delta: 10.71 (s, 1H) – 9, 9.04 (dd, J=4.98, 1.52Hz, 2H) – 2/4, 8.28 (dd, J=4.96, 1.54Hz, 2H) -1/5, 7.71 (m, 1H) – 14, 7.57 (ddd, J=7.64, 1.53, 0.72Hz, 1H) – 12, 7.38 (t, 1H) – 13, 4.41 (s, 12H N+-H protone – fast chemical exchange with water molecules) – 3, 3.72 (s, 3H) – 20, 2.30 (s, 3H) -16. 13C NMR (151MHz, d-DMSO, ppm) delta: 166.32-17, 162.88-7, 146.52-2/4, 145.42-6, 136.54-11, 134.61-10, 134.33-12, 128.25-15, 127.95-14, 126.95-13, 123.44-1/5, 52.10-20, 17.86-16.

According to the analysis of related databases, 22223-49-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kwiatek, Dorota; Kubicki, Maciej; Barczy?ski, Piotr; Lis, Stefan; Hnatejko, Zbigniew; Journal of Molecular Structure; vol. 1145; (2017); p. 86 – 93;,
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Electric Literature of 22223-49-0, The chemical industry reduces the impact on the environment during synthesis 22223-49-0, name is Methyl 2-amino-3-methylbenzoate, I believe this compound will play a more active role in future production and life.

Example 64 – Preparation of methyl 3-methyl-N-(6-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate Methyl 3-methylanthranilate (2.1 g, 13 mmol) was dissolved in 4 ml pyridine and 6-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl chloride was added. After a mild exothermic reaction subsided the reaction mixture was stirred at 50C for 24 hours. The pyridine was removed by evaporation at reduced pressure and the residue was treated with in 10% aqueous sodium bicarbonate. Insouble material was collected by filtration, washed with ether and dried to yield 2.9 (63%) of the desired product as a solid, mp 198.5-205C. An analytical sample was prepared by recrystallization from ethanol to yield a crystalline solid, mp 208.5-210.5C. IR and 1H NMR spectra were in agreement with the assigned structure.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 2-amino-3-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE DOW CHEMICAL COMPANY; EP142152; (1991); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 22223-49-0, name is Methyl 2-amino-3-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H11NO2

To a solution of methyl 2-amino-3-methylbenzoate (4) (1.00 g, 6.10 mmol) in DMF (10 ml) was added NBS (1.10 g, 6.10 mmol), and the reaction mixture was stirred at rt for 6 h. The reaction mixture was diluted with EtOAc (10 ml) and washed with saturated aqueous Na2CO3 solution (10 ml * 3). The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexanes/EtOAc = 100:1) to give compound 5 as pale gray solid (0.93 g, 62% yield): 1H NMR (400 MHz, CDCl3) delta (ppm) 7.88 (d, J = 2.3 Hz, 1H), 7.28 (d, J = 2.3 Hz, 1H), 5.82 (s, 2H), 3.86 (s, 3H), 2.15 (s, 3H).

According to the analysis of related databases, 22223-49-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kim, Mi Kyoung; Shin, Heerim; Cho, Seo Young; Chong, Youhoon; Bioorganic and Medicinal Chemistry; vol. 22; 3; (2014); p. 1156 – 1162;,
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Ester – an overview | ScienceDirect Topics

Electric Literature of 22223-49-0, A common heterocyclic compound, 22223-49-0, name is Methyl 2-amino-3-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.

A solution of sodium nitrite (1.9 g, 27.6 mmol) in water (5 ml) was added dropwise to an ice-cooled solution of methyl 2-amino-3-methyl benzoate (U.S. Pat. No. 4,657,893 preparation II) (4.14 g, 25 mmol) in acetic acid (50 ml). This solution was then added dropwise to a solution of tert-butyl mercaptan (2.26 g, 25 mmol) in ethanol (70 ml) and stirred at room temperature. The pH of the mixture was adjusted to 5.5 using saturated sodium carbonate solution and the mixture poured into brine. This mixture was extracted with ethyl acetate, the combined organic extracts dried (Na2SO4), concentrated under reduced pressure and the residue azeotroped with dichloromethane and heptane. The residue was dissolved in dimethyl sulphoxide (40 ml) and added dropwise to a suspension of potassium tert -butoxide (14.05 g, 126 mmol) in dimethyl sulphoxide (150 ml), and the reaction stirred at room temperature for 2 hours. The reaction was poured carefully into 1N hydrochloric acid, and extracted with ethyl acetate. The combined organic extracts were washed with 1N hydrochloric acid, dried (Na2SO4) and evaporated under reduced pressure. The product was slurried with isopropanol, sufficient dichloromethane added for complete dissolution, and the solution allowed to evaporate. The resulting solid was filtered off, washed with isopropanol to afford the title compound as an off-white solid. Microanalysis found: C, 59.26; H, 3.73; N, 17.28. C8H6N2O2 requires C, 59.31; H, 3.51; N, 17.42%. aa0-5aa Mpt. 230-233 C.

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; Barber, Christopher Gordon; Bunnage, Mark Edward; Harvey, John Wilson; Mathias, John Paul; US2005/20611; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics