Category: 55289-36-6

Reference of 55289-36-6, 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. 55289-36-6, name is 3-Bromo-2-methylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of sodium sulfate (61 .1 g, 430 mmol), hydroxylamine hydrochloride (8.96 g, 129 mmol), 2,2,2-trichloro-1 -ethoxyethanol (9.98 g, 51 .6 mmol) and 3-bromo-2- methylaniline (8 g, 43 mmol) in water (300 ml_) was added hydrochloric acid (3.92 ml_, 129 mmol) slowly. This mixture was heated to 90 C for 1 hr. The reaction was cooled, filtered and the solid was washed with water and dried to give 6-bromo-7- methylindoline-2,3-dione (8.6g, 35.8 mmol, 83 % yield) as a brown solid.

The synthetic route of 3-Bromo-2-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; JIN, Qi; POHLHAUS, Denise Teotico; SPLETSTOSER, Jared; (320 pag.)WO2017/98440; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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 55289-36-6 as follows. Recommanded Product: 55289-36-6

N-(3-Bromo-2-methyl-phen l)-2-hydroxyimino-acetamide A mixture of 3-Bromo-2-methyl-phenylamine (15.6 g, 0.084 mol), NH2OH H2S04 (71.25 g, 0.5 mol), cone. HC1 (8.8 mL) in H20 (90 mL) is slowly added to a solution of chloral hydrate (15.2 g, 0.09 mol), Na2S04 (71.25 g ,0.44 mol) in H20 (255 mL) then stirred at 35C for lh, 52 C for 1.5h, 75 C for lh. After the reaction, the mixture is filtered and the solid is dried under vacuum to give product. Yield: 18 g (83%)

According to the analysis of related databases, 55289-36-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ENGELHARDT, Harald; GIANNI, Davide; MANTOULIDIS, Andreas; SMETHURST, Christian; WO2014/154760; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 55289-36-6, These common heterocyclic compound, 55289-36-6, name is 3-Bromo-2-methylaniline, 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 triphosgene (2.249 g, 7.58 mmol) in toluene (26.9 mL) was stirred on an ice-water bath and treated slowly with a solution of 3-bromo-2-methylaniline (3 g,16.12 mmol) and DIEA (5.63 mL, 32.2 mmol) in toluene (5.37 mL). The resulting suspension was stirred at room temperature for 2 h, filtered, and the precipitate was washed with EtOAc. The combined filtrates were washed quickly with brine, dried and concentrated to provide 1 -bromo-3 -isocyanato-2-methylbenzene as a brown solid/oil mixture (3.36 g). Treatment of a portion of this crude material with ethanol provided 1-(3-bromo-2-methylphenyl)-3-ethylurea as an off-white solid. Mass spectrum m/z 357,259 (M+H). ?H NMR (400 MHz, DMSO-d6) oe 7.80 (s, 1H), 7.75 (d, J=7.5 Hz, 1H), 7.24(dd,J7.9, 0.9 Hz, 1H), 7.04 (t,J8.0 Hz, 1H), 6.50 (t,J5.4 Hz, 1H), 3.11 (qd,J=7.2,5.6 Hz, 2H), 1.07 (t, J7.3 Hz, 3H).

Statistics shows that 3-Bromo-2-methylaniline is playing an increasingly important role. we look forward to future research findings about 55289-36-6.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; AHMAD, Saleem; BATT, Douglas G.; LIU, Qingjie; MACOR, John E.; TINO, Joseph A.; WATTERSON, Scott Hunter; NAIR, Satheesh Kesavan; MAISHAL, Tarun Kumar; (247 pag.)WO2016/65236; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 55289-36-6, A common heterocyclic compound, 55289-36-6, name is 3-Bromo-2-methylaniline, molecular formula is C7H8BrN, 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.

Intermediate 32C: N-(3-Bromo-2-methylphenyl)-2-(3-methoxypyridin-2-yl)acetamide A mixture of sodium 2-(3-methoxypyridin-2-yl)acetate (0.166 g, 0.871 mmol), 3-bromo-2-methylaniline (0.118 mL, 0.958 mmol), DIEA (0.608 mL, 3.48 mmol) and HATU (0.397 g, 1.05 mmol) in DMF (4.0 mL) was stirred at room temperature. After 1 h, the mixture was diluted with EtOAc and washed twice with 10% aqueous LiCl, then with brine, dried and concentrated. The residue was purified by column chromatography on silica gel to provide N-(3-bromo-2-methylphenyl)-2-(3-methoxypyridin-2-yl)acetamide as a pale yellow solid (0.213 g, 73% yield). Mass spectrum m/z 335, 337 (M+H)+.

The synthetic route of 55289-36-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Batt, Douglas G.; Bertrand, Myra Beaudoin; Delucca, George; Galella, Michael A.; Ko, Soo Sung; Langevine, Charles M.; Liu, Qingjie; Shi, Qing; Srivastava, Anurag S.; Tino, Joseph A.; Watterson, Scott Hunter; US2014/378475; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 55289-36-6, name is 3-Bromo-2-methylaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H8BrN

[0249] (a) 4-Bromoindazole. A 350 mL 5-necked flask was charged with benzene (127 mL) and potassium acetate (4.24 g, 43.2 mmol). 3-Bromo-2- methyl-aniline (6.00 g, 42.4 mmol) was added over a period of 5 min to the white suspension followed by acetic anhydride (12.0 mL, 127 mmol). A thick white suspension was formed at this point. The mixture was heated to 80C and isopentyl nitrite (8.46 g, 43.2 mmol) was added and the orange suspension was heated at 80C overnight. The reaction mixture was cooled, filtered and the filter cake was washed with benzene (3×30 mL). The filtrate was concentrated under reduced pressure to remove the solvent and the residue was heated to 60C. Cone. HCl (2.0 mL) was added and the mixture was stirred at 7O0C for 1 h. More cone. HCl was added (2.0 mL) and the mixture was stirred at 70C for 3 h. The mixture was cooled, diluted with water and toluene until the solid was completely dissolved. The layers were separated and the aqueous layer was extracted with toluene (3×50 mL). The combined organics were concentrated until product began to crystallize. The suspension was cooled to 0C and the precipitated solid was filtered to provide 4-bromoindazole as a beige solid (4.45 g, 53%).

The synthetic route of 55289-36-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LOCUS PHARMACEUTICALS, INC.; WO2008/8059; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

55289-36-6, name is 3-Bromo-2-methylaniline, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 55289-36-6

To a solution of 10.0 g (53.7 mmol, 1.0 eq.) of 3-bromo-2-methylamine (LXXXVIIa) in 200 mL of acetonitrile at 0 C was added 42 mL of cone. HC1 followed by 42 mL of glacial acetic acid and a solution of 4.4 g (63.9 mmol, 1.1 eq.) of sodium nitrite in 12 mL of water. The mixture was purged with SO2 gas for 15 mm and a solution of 9.1 g (53.7 mmol, 1.0 eq.) ofcopper (II) chloride in 12 mL of water was added dropwise at 0 C. The mixture was allowed to warm to room temperature and stirred for 16 h. The mixture was concentrated in vacuo, diluted with 500 mL of water and extracted with 3 x 500 mL of ethyl acetate. The combined organic extracts were washed with 200 mL of sat. aqueous sodium bicarbonate solution, 200 mL of brine, dried (Na2SO4), filtered and the solvent was removed in vacuo. The residue waspurified by trituration with pentane to provide 8.0 g (29.7 mmol, 55%) of 3-bromo-2- methylbenzene-1-sulfonyl chloride (LXXXVIIIa). ?H NIVIR (400 MFIz, CDC13): 8.07 (d, 1H), 7.92 (d, 1H), 7.28 (t, 1H), 2.88 (s, 3H).

Statistics shows that 55289-36-6 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-2-methylaniline.

Reference:
Patent; ARBUTUS BIOPHARMA CORPORATION; COLE, Andrew, G.; DORSEY, Bruce, D.; KAKARLA, Ramesh; KULTGEN, Steven; QUINTERO, Jorge; (353 pag.)WO2018/172852; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 55289-36-6, name is 3-Bromo-2-methylaniline, molecular formula is C7H8BrN, 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. 55289-36-6

To a solution of compound 298a (8g, 43mmol) in dichloromethane (80ml) at 0 C was added compound 298b (16ml, 113.5mmol). The reaction solution was stirred at 0 C for 30 minutes, and then solid potassium nitrate (5.43g, 53.7 mmol), the ice bath was removed, and the reaction solution was stirred at room temperature for 4 hours. LCMS monitored the reaction of the raw materials. The reaction solution was concentrated and dried under vacuum. The residue was added with water and extracted twice with dichloromethane (2 * 200 ml). The organic phases were combined, dried over anhydrous sodium sulfate, and filtered with suction.It was dried and the crude product was passed through the column to obtain a yellow solid compound (Example 298c, 4.0972g, yield 28.57%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 55289-36-6, its application will become more common.

Reference:
Patent; Jiaxing Tekeluo Biological Technology Co., Ltd.; Xing Li; Li Guanqun; Wang Xiaolei; Cai Yuting; Jiang Xiang; Pan Xiang; Zhu Wenhao; Wang Yang; Wang Zengquan; (83 pag.)CN110627775; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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 55289-36-6 as follows. 55289-36-6

General procedure: To a cooled solution of the chosen 2-methylaniline dissolved in HBF4 (50% solution in water; 15-30 mL) was added at 0 C dropwise a cooled aqueous solution of NaNO2 (1 equiv in the minimum of water). After the end of the addition, the mixture was stirred 1 h at 0 C and 2 h at room temperature. Then, the resulting precipitate was filtered, washed with Et2O (3 ¡Á 100 mL) and dried to obtain the corresponding 2-methylphenyldiazonium tetrafluoroborate salts which were directly added in one portion under nitrogen to a stirred mixture of KOAc (2 equiv) and 18-crown-6 (0.05 equiv) in dry CHCl3 (350-700 mL). After 2 h at room temperature, the mixture was filtered, washed with CHCl3 (3 ¡Á 100 mL) and the organic filtrate was finally concentrated in vacuo. The residual gum was purified by column chromatography on silica gel (EtOAc/cyclohexane 1:3) to give the desired indazoles 1 and 2a.

According to the analysis of related databases, 55289-36-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lohou, Elodie; Sopkova-De Oliveira Santos, Jana; Schumann-Bard, Pascale; Boulouard, Michel; Stiebing, Silvia; Rault, Sylvain; Collot, Valerie; Bioorganic and Medicinal Chemistry; vol. 20; 17; (2012); p. 5296 – 5304;,
Bromide – Wikipedia,
bromide – Wiktionary

55289-36-6, A common compound: 55289-36-6, name is 3-Bromo-2-methylaniline, belongs to bromides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

A mixture of 3-bromo-2-methylaniline (4.000g) , 4, 4, 4′, 4′, 5, 5, 5′, 5′-octamethyl-2, 2′-bi (1, 3, 2-dioxaborolane) (6.550g) and potassium acetate (4.220g) in 1, 4-dioxane (44.8mL) and DMSO (9.0mL) was purged with nitrogen for 10 min. [1, 1′-Bis (diphenylphosphino) ferrocene] -dichloropalladium DCM adduct (0.527g) was added, the mixture was purged for another 5min then was heated at reflux for 2h. The mixture was cooled and filtered through Celite. The solids were washed with EtOAc, and the combined filtrates were washed with water and brine, and dried and concentrated. The residue was purified by column chromatography (eluting with hexane-EtOAc using a gradient from 20: 1 to 85: 15) . 2-methyl-3- (4, 4, 5, 5-tetramethyl- 1, 3, 2-dioxaborolan-2-yl) aniline (compound M1) as a light yellow waxy solid (4.400g, 88%) .[0356]1H NMR (400 MHz, chloroform-d) delta 7.21 (1H, dd, J=7.3, 1.0 Hz) , 7.02 (1H, t, J=7.7 Hz) , 6.75 (1H, dd, J=7.8, 1.0 Hz) , 3.54 (2H, br. s. ) , 2.37 (3H, s) , 1.34 (12H, s) . Mass spectrum m/z 233.3, 234.3, 235.3 (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, 3-Bromo-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BETTA PHARMACEUTICALS CO., LTD; WANG, Yiqian; FU, Bang; ZHANG, Yao; LIU, Xiangyong; WANG, Jiabing; DING, Lieming; (103 pag.)WO2019/192506; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

55289-36-6, These common heterocyclic compound, 55289-36-6, name is 3-Bromo-2-methylaniline, 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.

Reference Example 19; 4-Bromo-2-trifluoromethyl-lJH-indoIe; A solution of 2-methyl-3-bromo-aniline (6.05 g, 37 mmol) in pyridine (8 mL) and DCM (150 mL) was cooled to 0 C and treated drop-wise with trifluoroacetic anhydride (11.5 mL, 81.4 mmol). The reaction mixture was stirred at RT for 2 h, then quenched with an aqueous solution of ammonium chloride. The organic layer was dried over MgSO4, and evaporated to dryness to give N-(3-bromo-2-methyl-phenyl)-2,2,2-trifluoro-acetamide as an off-white solid, which was used without further purification (10 g).NMR deltaH (400 MHz, CDCl3) 2.38 (s, 3H), 7.14 (apparent t, J = 8.0, IH), 7.53 (d, J = 8.0, IH),7.66 (d, J = 8.0, IH) and 7.75 (bs, IH).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 55289-36-6.

Reference:
Patent; PIRAMED LIMITED; THE INSTITUTE OF CANCER RESEARCH; WO2008/125835; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary