Category: 583-75-5

Electric Literature 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.

6-bromo-8-methylquinoline. Glycerol (2.3 ml, 32.2 mmol) was added dropwise via syringe to a solution of 4-bromo-2-methylaniline (5.00 g, 26.8 mmol) and sodium iodide (52 mg, 0.349 mmol) in 75% aq H2SO4 (15.81 ml, 120 mmol) at 140 C. The mixture was held at this temperature for 3 hours. The reaction mixture was neutralized to a pH of 7 with aq NaOH. This mixture was extracted with EtOAc and the combined organics were washed with brine, dried over MgSO4 and concentrated. Column chromatography on silica gel (5-25% EtOAc in hexanes) afforded intermediate 11 (5.50 g, 24.7 mmol, 92%). 1H NMR (400 MHz, CDCl3) delta ppm 8.93 (dd, J=4.28, 1.76 Hz, 1H), 8.03 (dd, J=8.31, 1.76 Hz, 1H), 7.82 (d, J=2.01 Hz, 1H), 7.65 (d, J=1.01 Hz, 1H), 7.40 (dd, J=8.18, 4.15 Hz, 1H), 2.78 (s, 3H). Mass 221 [M+H]+.

The synthetic route of 4-Bromo-2-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/18163; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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., Recommanded Product: 4-Bromo-2-methylaniline

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

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. Computed Properties of 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.

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

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5688810; (1997); A;; ; Patent; Ligand Pharmaceuticals Incorporated; US5696127; (1997); A;,
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. 583-75-5, name is 4-Bromo-2-methylaniline, A new synthetic method of this compound is introduced below., Product Details of 583-75-5

Adding the compound 183a (1.0 g, 5.37 mmol),Compound 183b (2.73 g, 10.75 mmol),Potassium acetate (1.58 g, 16.12 mmol) and PdCl2 (dppf) (0.39 g, 0.54 mmol) were added to 1,4-dioxane (20 mL), replaced with nitrogen three times, and then stirred at 90 C for 4 hours. The reaction solution was cooled to room temperature and filtered.The filter cake was washed with ethyl acetate (15 mL × 2), and the filtrate was concentrated.The concentrate was purified by silica gel chromatography (ethyl acetate: petroleum ether = 0-80%) to obtain a compound 183c as a yellow solid, namely , 2-Dioxoranepentyl-2-yl) aniline (1.21 g, 96.6% yield).

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; 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

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., name: 4-Bromo-2-methylaniline

Preparation #4: 2-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine A mixture of 4-bromo-2-methylaniline (0.250 g, 1.34 mmol), bis(pinacolato)diboron (0.442 g, 1.747 mmol), dichloro[1,1’bis(diphenylphosphino)-ferrocene]palladium (II) dichloromethane adduct (0.110 g, 0.134 mmol), and potassium acetate (0.329 g, 3.357 mmol) was heated in N,N-dimethylformamide (5 mL) at about 80 C. for about 15 h under an atmosphere of nitrogen. The mixture was allowed to cool to ambient temperature and was purified by flash column chromatography on silica gel using ethyl acetate/heptane (3:7) as the mobile phase to give 2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine as a yellow oil (0.213 g, 0.914 mmol); RP-HPLC (25% to 100% acetonitrile/0.1 M aqueous ammonium acetate, buffered to pH 4.5, over 10 min at 1.0 mL/min; lambda=254 nm; Hypersil C18, 100 A, 5 mum, 250*4.6 mm column) Rt 11.02 min.

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; Wishart, Neil; Friedman, Michael; Arnold, Lee D.; Yang, Bryant; Fix-Stenzel, Shannon R.; Ericsson, Anna; Michaelides, Michael R.; Qian, Xiao-Dong; Holms, James H.; Steinman, Douglas H.; Tian, Zhengping; Wittenberger, Steven J.; US2006/25383; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature 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.

To a solution of 4-bromo-2-methylaniline (1 g, 5.37 mmol,) in 1,4-dioxane (11 mL) and H2O (4 mL), at r. t. , were added Et3N (2.7 mL, 1.2 eq) and BOC20 (4.2 g, 1.2 eq). The reaction mixture was stirred at r. t. for 96 hr. Sat. aq. NH4CI and EtOAc (20 mL) were added and the phases were separated. The aqueous layer was further extracted with EtOAc (2X20 mL). The combined organic extracts were dried over anh. NA2SO4, the solids were filtered and the solvent evaporated. The residue was purified by SCX Column (Eluents : CH2CI2, MeOH and NH3 (0.5 M in MEOH)) to give the title compound as a white solid (1.22 g, 79%). NMR (‘H, DMSO-D6) : 8 8.55 (s, 1H), 7.35 (m, 1H), 7.28 (m, 2H), 2.17 (s, 3H), 1.44 (s, 9H). MS (m/z) : 230 [MH-TBU] + ; 186 [MH-BOC] +.

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

Reference:
Patent; SB PHARMCO PUERTO RICO INC; NEUROCRINE BIOSCIENCES INC; GLAXO GROUP LIMITED; WO2004/62665; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application 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.

Compound 13-2 (0405) To a mixture of 4-bromo-2-methylbenzenamine (500 mg, 2.69 mmol), KOAc (1.32 g, 13.4 mmol) and bis(pinacolato)diboron (2.05 mg, 8.0 mmol) in dioxane (4 mL) was added Pd(dppf)Cl2 (110 mg, 0.134 mmol). After having been degassed and recharged with nitrogen, the mixture was refluxed at 85 C. for 16 h. TLC showed that the reaction was complete. Water (20 mL) was added and the mixture was extracted with ethyl acetate (30 mL×3). The combined organic layers were dried over Na2SO4, filtered, concentrated and purified by silica gel column chromatography (DCM) to afford 13-2 as a white solid (485 mg, yield 77%).

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

Reference:
Patent; Nivalis Therapeutics, Inc.; Wasley, Jan; Rosenthal, Gary J.; Sun, Xicheng; Strong, Sarah; Qiu, Jian; US9138427; (2015); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products 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.

In a 100 niL 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 was cooled 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 EtO Ac were added to separate the phases and the aqueous phase was extracted with EtO Ac. 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, 1H), 7.38-7.28 (m, 2H), 7.15-7.02 (m, 1H), 2.27 (s, 3H), 1.57-1.48 (m, 1H), 1.10 (quint, J = 3.9 Hz, 2 H), 0.92-0.79 (m, 2H); MS ESI [M + H]+ 253.9, calcd for [CnHi2BrNO + H]+ 254.0.

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; UNIVERSITY HEALTH NETWORK; LAUFER, Radoslaw; NG, Grace; LI, Sze-Wan; PAULS, Heinz W.; LIU, Yong; PATEL, Narendra Kumar B.; WO2015/70349; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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.

A mixture of 4-bromo-2-methylaniline (0.0268 mol), intermediate E3, palladium (0) acetate (0.00537 mol), tri-o-tolylphosphine (0.0268 mol) and acrylonitrile (0.0896 mol) in triethylamine (0.107 mol) and acetonitrile (70 ml) was stirred at 140C in a stainless-steel bomb for 18h. After cooling, the mixture was filtered over celite and the filtrate was poured in water and extracted with CH2Cl2. The organic layer was dried over magnesium sulfate, filtered and the solvent evaporated. The residue was purified by column EPO chromatography over silica gel (eluent: CHiCyCyclohexane 50/50; 35-70 mum). The pure fractions were collected and the solvent evaporated. Yield: 3.2 g of intermediate F3 (75 %, melting point : 105C)

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; TIBOTEC PHARMACEUTICALS LTD.; ARTS, Frank Xavier Jozef Herwig; WO2006/45828; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 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.

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.

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

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5693647; (1997); A;,
Bromide – Wikipedia,
bromide – Wiktionary