The important role of 583-75-5

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-2-methylaniline, its application will become more common.

Electric Literature of 583-75-5,Some common heterocyclic compound, 583-75-5, name is 4-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.

Potassium acetate (317 mg, 3.22 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (300 mg, 1.18 mmol) and 4-bromo-2-methyl-aniline (200 mg, 1.08 mmol) were dissolved in dimethylsulfoxide (3 mL). The reaction mixture was degassed using argon. 1,1′-Bis-diphenylphosphine ferrocene palladium(II) dichloride (24 mg, 0.03 mmol) was added and the reaction mixture was heated at 80 C for 5 h. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (20 mL). The organic layer was washed with saturated sodium bicarbonate (20 mL) and brine (20 mL). The organic layer was dried with sodium sulfate, filtered and purified by flash silica column chromatography (heptane:ethyl acetate, 0-40%) to obtain a crude mixture of starting material and product. The mixture was purified using reversed phase column chromatography to obtain the title compound as a clear oil (50 mg, 21%). ESI-MS m/z: 234 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-2-methylaniline, its application will become more common.

Reference:
Patent; Emergent Product Development Gaithersburg Inc.; Roussel, Patrick; Heim, Jutta; Schneider, Peter; Bartels, Christian; Liu, Yaoquan; Dale, Glenn; Milligan, Daniel; (107 pag.)EP3034078; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Extended knowledge of 583-75-5

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2-methylaniline, and friends who are interested can also refer to it.

Reference of 583-75-5, 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. 583-75-5 name is 4-Bromo-2-methylaniline, 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.

Step A: ammonium tetrafluoroborate (20.97 g, 200 mmol) was dissolved in aqueous acetic acid (500 ML AcOH/250 ML water) and cooled to 0 C. 2-Methyl-4-bromoaniline (18.61 g, 100 mmol) and 42 ML of aqueous concentrated HCl (36% w/w, 12N, 500 mmol) were sequentially added.The mixture was stirred for 20 minutes at 0 C. and NaNO2 (7.59 g, 110 mmol) was added.The reaction was stirred for 1 hour at 0 C. and warmed to room temperature.After 16 hours at room temperature, the mixture was concentrated under reduced pressure and the residue was azeotroped with toluene and dried under high vacuum.The solid was suspended in 500 ML of CHCl3 and KOAc (12.76 g, 130 mmol) and 18-crown-6 (7.93 g, 30 mmol) were added.The reaction was stirred for 1.5 hours at room temperature.The mixture was washed with water, dried over anhydrous MgSO4, filtered through Celite and concentrated under reduced pressure to provide 30 g of 5-bromo-1H-indazole (compound 2f) as a tan solid.The crude material was used without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; Munson, Mark; Rizzi, James; Rodriguez, Martha; Kim, Ganghyeok; US2004/176325; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

New learning discoveries about 583-75-5

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, 4-Bromo-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Synthetic Route of 583-75-5, 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. 583-75-5, name is 4-Bromo-2-methylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 192 1,2-Dihydro-6-(3-nitrophenyl)-2,2,4,8-tetramethylquinoline (Compound 292, structure 86 of Scheme XXII, where R1 =R3-5 =H, R2 =nitro) 4-Bromo-2-methylaniline (5.58 g, 30 mmol) was treated with iodine (0.2 g, 0.9 mmol) and acetone (150 mL) in a sealed tube at 80 C. for 24 h to provide 6-bromo-1,2-dihydro-8-methylquinoline (Compound 85 of Scheme XXII) in 9 % yield as a yellow oil (0.70g). Most of the aniline (>80%) was recovered.

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, 4-Bromo-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5696133; (1997); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Research on new synthetic routes about 583-75-5

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 of 583-75-5, A common heterocyclic compound, 583-75-5, name is 4-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.

In a 100 mL RBF, 4-bromo-2-methylaniline (3.7 g, 20 mmol) and DIPEA (6.95 mL, 40 mmol) were combined with DMF (40 mL). The reaction wascooled to 0 C in an ice bath and cyclopropanecarbonyl chloride (2.1 g, 20 mmol) was added. The mixture was stirred at 0 C for 1 h. Water and EtOAc were added to separate the phases and the aqueous phase was extracted with EtOAc. The organic layers were combined, dried over Na2S04, filtered, and concentrated under reduced pressure to give the title compound as a white solid (4.76 g, 94%). NMR (400 MHz, CDCl3) delta ppm 7.85-7.72 (m, 1 H), 7.38-7.28 (m, 2H), 7.15-7.02 (m, l H), 2.27 (s, 3H), 1.57- 1.48 (m, 1 H), 1.10 (quint, J = 3.9 Hz, 2 H), 0.92-0.79 (m, 2H); MS ESI [M + H]+253.9, calcd for [C, ,H12BrNO+H]+254.0.

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; UNIVERSITY HEALTH NETWORK; LIU, Yong; PAULS, Heinz W.; LAUFER, Radoslaw; LI, Sze-Wan; SAMPSON, Peter Brent; FEHER, Miklos; NG, Grace; PATEL, Narendra Kumar B.; LANG, Yunhui; WO2014/75168; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Brief introduction of 583-75-5

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 583-75-5.

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. 583-75-5, name is 4-Bromo-2-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H8BrN

EXAMPLE 192 1,2-Dihydro-6-(3-nitrophenyl-2,2,4,8-tetramethylquinoline (Compound 292, Structure 86 of Scheme XXII, where R1 =R3-5 =H, R2 -nitro) 4-Bromo-2-methylaniline (5.58 g, 30 mmol) was treated with iodine (0.2 g, 0.9 mmol) and acetone (150 mL) in a sealed tube at 80 C. for 24 h to provide 6-bromo-1,2-dihydro-8-methylquinoline (Compound 85 of Scheme XXII) in 9% yield as a yellow oil (0.70 g). Most of the aniline (>80%) was recovered.

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 583-75-5.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5693646; (1997); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Continuously updated synthesis method about 583-75-5

The synthetic route of 583-75-5 has been constantly updated, and we look forward to future research findings.

583-75-5, name is 4-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. Safety of 4-Bromo-2-methylaniline

To a solution of compound 220-Si (5 g, 26.88 mmol) in EtOH (100 mL) was added 12(6.828 g, 26.88 mmol) and Ag2SO4 (8.3 82 g, 26.88 mmol). The mixture was stirred at room temperature overnight. The mixture was quenchedwith aqueous Na2S2O3 solution and extracted with EtOAc (2x). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, and concentrated. The residue was purified by column chromatography on silica gel eluted with petroleum ether to afford compound 220-S2 (6.31 g, 75.5 %) as a light brown solid. LC/MS (ESI) m/z: 312 (M+H) .

The synthetic route of 583-75-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; BARRISH, Joel, Charles; GREENLEE, William; EASTMAN, Kyle, J.; (0 pag.)WO2018/160889; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Extracurricular laboratory: Synthetic route of 583-75-5

The synthetic route of 583-75-5 has been constantly updated, and we look forward to future research findings.

Reference of 583-75-5,Some common heterocyclic compound, 583-75-5, name is 4-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.

4-bromo-2-methylaniline (5.0 g, 27 mmol) was added to a mixture of water (12.3 ml) and HBF4 (48% by weight in water, 12.3 ml, 67 mmol) in a Nalger reaction vessel cooled in an ice water bath. Then, NaNO2 (1.85 g, 27 mmol) in water (3.8 ml) was added while maintaining the temperature of the reaction around 10 C. After 15 minutes, the was then recooled in an ice water bath and filtered via a Buchner funnel. The solid was washed with cold 5% aqueous HBF4, cold MeOH (20 ml) and diethyl ether (3 x 10 ml). The solid was dried on a Buchner funnel for 1 hour and then added to a flask containing KOAc (5.3 g, 54 mmol, dried in vacuo overnight) and 18-C-6 (0.35 g, 1,3 mmol) suspended in chloroform (250 ml). The reaction was stirred at room temperature for 2 hours and then filtered, and the solid was washed with chloroform. The filtrate was washed with water and brine, dried over sodium sulfate, filtered, concentrated, and diluted with water (250 ml). The suspension was filtered, and the solid was washed with hexanes (50 ml) and diethyl ether (50 ml), collected, and dried in vacuo to give title compound (3.6 g, 68%). MS (ESI pos. ion) m/z: 197 (M+H). Calc’d Exact Mass for C7H5BrN2: 196.

The synthetic route of 583-75-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2007/5668; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Extended knowledge of 583-75-5

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 583-75-5.

583-75-5, These common heterocyclic compound, 583-75-5, name is 4-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.

3,6-Dibromotoluene In a 2000 ml beaker containing 400 ml of 23percent aqueous HBr, 46.5 g (0.25 mol) of melted 2-methyl-4-bromoaniline was slowly added. This mixture was stirred for 20 minutes using a mechanical stirrer, then cooled to -5¡ã C. Then a solution of 22.4 g (0.33 mol) of NaNO2 in 130 ml of water was added dropwise over 1 hour at this temperature. The diazonium reagent obtained was added in several portions to a solution of 35.9 g (0.25 mmol) of CuBr in 100 ml of 47percent HBr at 0¡ã C. The resulting mixture was warmed to 70¡ã C., stirred for 30 minutes at this temperature, and, then, cooled to room temperature. The product was extracted with 3*200 ml of methyl-tert-butyl ether. The combined extract was dried over K2CO3 and evaporated to dryness. Firstly, the crude product was purified using short column with Silica Gel 60 (40-63 mum, d 60 mm, 140 mm; eluant: hexanes). Fractional distillation gave colorless oil, b.p. 100-102¡ã C./10 mm Hg. Yield, 36.1 g (58percent). Anal. calc. for C7H6Br2: C, 33.64; H, 2.42. Found: C, 33.79; H, 2.50. 1H NMR (300 MHz, CDCl3): delta 7.39 (m, 1H, 5-H), 7.37 (m, 1H, 3-H), 7.18 (m, 1H, 6-H), 2.38 (s, 3H, Me). 13C NMR (75 MHz, CDCl3): delta 139.9, 133.6, 133.5, 130.3, 123.5, 120.9, 22.7.

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 583-75-5.

Reference:
Patent; Voskoboynikov, Alexander Z.; Izmer, Vyatcheslav V.; Asachenko, Andrey F.; Nikulin, Mikhail V.; Ryabov, Alexey N.; Lebedev, Artyom Y.; Coker, Catalina L.; Canich, Jo Ann M.; US2007/135597; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary