Category: 59557-91-4

Electric Literature of 59557-91-4, 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. 59557-91-4, name is 4-Bromo-2-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Embodiment 8A 4-Bromo-2-methoxy-5-nitroaniline 2-Methoxy-4-bromoaniline (5.00g, 24.75mmol) was added to concentrated H2SO4 (50mL) at 0 to 5C and then guanidine nitrate (3.02g, 24.75mmol) was added in batches. The mixture was stirred at 0 to 5C for 30 minutes. TLC showed the reaction was complete and the reaction mixture was slowly added dropwise to a solution of NaHCO3 (100g) in water (1L), the temperature was controlled below 15C. The resulting mixture was filtered to deliver the title compound (yellow solid, 5.40g, yield 83.90%). 1H NMR (400MHz, CDCl3): delta, 7.39 (s, 1H), 7.01 (s, 1H), 4.09 (br. s., 2H), 3.96 (s, 3H).

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-methoxyaniline, other downstream synthetic routes, hurry up and to see.

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. 59557-91-4, name is 4-Bromo-2-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 4-Bromo-2-methoxyaniline

At room temperature, concentrated sulfuric acid (185 mL) and deionized water (144 mL) were added with mechanical stirring in a three-necked flask.Glycerol (768.5 mmol, 207.5 g) was added and the temperature was lowered to room temperature. Sodium 3-nitrobenzenesulfonate (733 mmol, 165 g) was added in portions and the reaction was carried out at 80 C for 3 hours, 4-bromo-2-methoxyaniline (compound shown by the formula (I-1)) (495 mmol, 100.0 g) was added portionwise with vigorous stirring to giveHeat to 120 C and react overnight. Add water (600 mL) and adjust pH to approx. 7.0 with concentrated aqueous ammonia. Extract with water and ethyl acetateAfter the extraction, the organic phase was dried over anhydrous sodium sulfate, filtered, and the solvent was spinned to give 103 g of tan by column chromatographyThe oily product (compound represented by the formula (I)) had a yield of 87.4% and a purity of 94%.

The synthetic route of 59557-91-4 has been constantly updated, and we look forward to future research findings.

Application of 59557-91-4, 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. 59557-91-4 name is 4-Bromo-2-methoxyaniline, 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.

4-Bromo-2-methoxyaniline (2.00 g, 9.90 mmol) were dissolved in water (10 mL) and concentrated hydrochloric acid (3 mL). The mixture was cooled in ice-salt bath, then a solution of sodium nitrite (0.69 g, 9.8 mmol) in water (4 mL) was added dropwise slowly while maintaining the temperature at 0-5 C. After the addition, the mixture was stirred at 0C for 5 min. The mixture described above was added to a mixture of sodium acetate trihydrate (8.75 g, 64.3 mmol), ethyl isocyanoacetate (1.0 mL, 9.15 mmol) and MeOH/H2O (22 mL, 10/1) while maintaining the temperature at 0-5 C. After the addition, the mixture was stirred at 0C for 30 min, then warmed to rt for further 3 h. After the reaction was completed, the mixture was concentrated to remove most of the solvent. The residue was filtered, and the filter cake was washed with cool water. The filter cake was dried in vacuo to give a reddish brown solid (2.65 g, 82.1%). MS (ESI, pos.ion) m/z: 327.1 (M+2)

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

Reference:
Patent; Sunshine Lake Pharma Co., Ltd.; WANG, Xiaojun; ZHOU, Pingjian; YANG, Chuanwen; HUANG, Changwei; XIONG, Shaohui; ZHANG, Yingjun; ZHANG, Jiancun; (139 pag.)EP3342765; (2018); A1;,
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Application of 59557-91-4, 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. 59557-91-4 name is 4-Bromo-2-methoxyaniline, 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.

4-Bromo-2-methoxyaniline (2.00 g, 9.90 mmol) were dissolved in water (10 mL) and concentrated hydrochloric acid (3 mL). The mixture was cooled in ice-salt bath, then a solution of sodium nitrite (0.69 g, 9.8 mmol) in water (4 mL) was added dropwise slowly while maintaining the temperature at 0-5 C. After the addition, the mixture was stirred at 0C for 5 min. The mixture described above was added to a mixture of sodium acetate trihydrate (8.75 g, 64.3 mmol), ethyl isocyanoacetate (1.0 mL, 9.15 mmol) and MeOH/H2O (22 mL, 10/1) while maintaining the temperature at 0-5 C. After the addition, the mixture was stirred at 0C for 30 min, then warmed to rt for further 3 h. After the reaction was completed, the mixture was concentrated to remove most of the solvent. The residue was filtered, and the filter cake was washed with cool water. The filter cake was dried in vacuo to give a reddish brown solid (2.65 g, 82.1%). MS (ESI, pos.ion) m/z: 327.1 (M+2)

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

Reference:
Patent; Sunshine Lake Pharma Co., Ltd.; WANG, Xiaojun; ZHOU, Pingjian; YANG, Chuanwen; HUANG, Changwei; XIONG, Shaohui; ZHANG, Yingjun; ZHANG, Jiancun; (139 pag.)EP3342765; (2018); A1;,
Ether – Wikipedia,
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Some common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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. name: 4-Bromo-2-methoxyaniline

a) tert-Butyl N-(4-bromo-2-methoxyphenyl)carbamate. A mixture of 4-bromo-2-methoxyaniline (34.0 g, 0.17 mol) and di-tert-butyl dicarbonate (44.5 g, 0.20 mol) in tetrahydrofuran (350 ml) was heated at reflux for 22 h. The mixture was allowed to cool to ambient temperature and the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (350 ml) and washed with 1 N citric acid (200 ml), dried over magnesium sulfate, filtered and evaporated to give tert-butyl N-(4-bromo-2-methoxyphenyl)carbamate as a yellow oil (80% pure, 57.10 g, 0.15 mol): 1H NMR (DMSO-d6, 400 MHz) delta 8.01 (s, 1H), 7.63 (d, 1H), 7.17 (d, 1H), 7.07 (dd, 1H), 3.82 (s, 3H), 1.45 (s, 9H); TLC (n-heptane/ethyl acetate=2:1) Rf 0.67.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 59557-91-4, its application will become more common.

Reference:
Patent; CALDERWOOD, DAVID; ARNOLD, LEE; MAZDIYASNI, HORMOZ; HIRST, GAVIN C.; DENG, BOJUAN B.; JOHNSTON, DAVID N.; RAFFERTY, PAUL; TOMETZKI, GERALD B.; TWIGGER, HELEN L.; MUNSCHAUER, RAINER; US2003/187001; (2003); A1;,
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Related Products of 59557-91-4, A common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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.

General procedure: To a solution of 4-bromo-2-methoxyaniline (11a) (300 mg, 1.48 mmol) in anhydrous CH2Cl2(15 mL) was added pyridine (0.24 mL, 2.97 mmol) and 1-propanesulfonyl chloride (0.18 mL, 1.63 mmol) under an argon atmosphere.The mixture was stirred at room temperature for 16 h.After being quenched with 1 N HCl(aq) (1.0 mL), water and CH2Cl2were added and then the layers were separated. The combinedorganic phases were washed with brine, dried over anhydrousNa2SO4, filtered and concentrated. The residue was purified bycolumn chromatography on silica gel (EtOAc/hexane, 10:90 to15:85) to give 13a (490.1 mg, 99%) as a light yellow oil.

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:
Article; Bufton, Joshua C.; Bullock, Alex N.; Cuny, Gregory D.; Dai, Bing; Degterev, Alexei; Duddupudi, Anantha Lakshmi; Gyrd-Hansen, Mads; Hu, Ming; Li, Li; Pinkas, Daniel M.; Schlicher, Lisa; Suebsuwong, Chalada; European Journal of Medicinal Chemistry; vol. 200; (2020);,
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These common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-methoxyaniline, 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. Quality Control of 4-Bromo-2-methoxyaniline

EXAMPLE 175B tert-butyl 4-bromo-2-methoxyphenylcarbamate A mixture of Example 175A (36.4 g, 180 mmol), and di-tert-butyl dicarbonate (47.2 g, 216 mmol) in THF (500 mL) was heated to reflux for 20 hours and cooled to ambient temperature. HPLC (using the conditions from Example 175A, product Rt=13.55 min and TLC (8:2 heptane/ethyl acetate, Rf of product=0.53, Rf of 4-bromo-2-methoxyaniline=0.27) indicated approximately 10% starting material was remaining. Additional di-tert-butyl dicarbonate (3.9 g, 18 mmol) was added and heating was continued for another 5 hours. The mixture was cooled and evaporated under reduced pressure. The residue was applied to a 400 gram silica gel column and eluted with 8:2 heptane/ethyl acetate. The fractions showing the desired product were combined and washed with saturated NaHCO3 and then brine. The organic solution was dried (MgSO4), filtered, and concentrated to provide 61.3 g of a mixture of the desired product and di-tert-butyl dicarbonate which was used directly in the next step.

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

Reference:
Patent; Betschmann, Patrick; Burchat, Andrew F.; Calderwood, David J.; Curtin, Michael L.; Davidsen, Steven K.; Davis, Heather M.; Frey, Robin R.; Heyman, Howard R.; Hirst, Gavin C.; Hrnciar, Peter; Michaelides, Michael R.; Muckey, Melanie A.; Rafferty, Paul; Wada, Carol K.; US2005/43347; (2005); A1;,
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Reference of 59557-91-4, 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. 59557-91-4, name is 4-Bromo-2-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 99 7-[(cyclopropylmethyl)amino]-5-{ [2-methoxy-4-(piperidin-4-yl)phenyl]amino}pyrido[3,4- d]pyridazin-4-ol EXAMPLE 99A itri-buty l 4-(4-amino-3-methoxyphenyl)-5,6-dihvdropyridine- l (2/J)-carbox late A mixture of 4-bromo-2-methoxybenzenamine ( 1.21 g, 6.0 mmol), tert-butyl 4- (3,3,4,4-tetramethylborolan-l-yl)-5,6-dihydropyridine- l (2/ )-carboxylate ( 1 .95 g. 6.3 mmol), sodium carbonate (1.91 g, 18 mmol) and 1, 1 ‘- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.22 g, 0.3 mmol) in dioxane (25 mL) and water (5 mL) was degassed with nitrogen and heated at 90C for 1 hours. After coohng to ambient temperature, the mixture was filtered, concentrated and purified by flash” chromatography eluting with 200: 1 dichloromethane/methanol to give the title compound.MS: 305 (M+rf).

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-2-methoxyaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI) COMPANY, LTD.; VASUDEVAN, Anil; PENNING, Thomas Dale; CHEN, Huanming; LIANG, Bo; WANG, Shaohui; ZHAO, Zhongqiang; CHAI, Dikun; YANG, Leifu; GAO, Yingxiang; WO2012/97682; (2012); A1;,
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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 59557-91-4 as follows. name: 4-Bromo-2-methoxyaniline

Step 1: To a solution of 4-bromo-2-methoxyaniline (2.0 g, 9.9 mmol) in MeCN (50 mL) was added para-toluenesulfonic acid (5.1 g, 27 mmol). The resulting mixture was cooled in an ice water bath. A solution of NaNO2 (1.36 g, 19.7 mmol) and KI (4.11 g, 24.8 mmol) in water (50 mL) was then added, and the resulting mixture was stirred for 5 min. The mixture was then removed from the ice water bath. Once consumption of starting material was observed, the reaction mixture was partitioned between water and EtOAc. The organic phase was concentrated and the resulting crude residue was purified by silica gel chromatography to afford 4-bromo-1-iodo-2-methoxybenzene

According to the analysis of related databases, 59557-91-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gilead Scientific Systems, Inc.; Cory, Kevin S; Doo, Jimin; Farrand, Julie; Guerrero, Juan A; Katana, Ashley A; Cato, Daryl; Laisaweed, Scott I; Lee, Jiayao; Lingco, John O; Nicolaus, May; Notte, Gregory; Phyen, Hyeoung-Jung; Sangy, Michael; Sumit, Arun C; Adam J, Surayyah; Stephens, Cork L; Venkatraman, Chandrasekar; Watkins, William J; Yang, Jong Yu; Jabloki, Jeff; Jifel, Shiela; Ro, Jennifer; Lee, Sung H; Jao, Chung Dong; Grove, Jeffery; Su, Jianjun; Blomgren, Peter; Mitchell, Scott A; Shyung, Jin Ming; Chandrasekar, Jayaraman; (460 pag.)KR2016/37198; (2016); A;,
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Adding a certain compound to certain chemical reactions, such as: 59557-91-4, name is 4-Bromo-2-methoxyaniline, belongs to ethers-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 59557-91-4, Recommanded Product: 4-Bromo-2-methoxyaniline

4-Bromo-2-methoxy-aniline (20 g, 99 mmol) was dissolved in water (695 mL) and concentrated sulphuric acid (113 ML). The solution was cooled to 0 C and sodium nitrite (7.5 g, 109 mmol) dissolved in water (32 mL) was added and stirred for 1 hour at 5-10 C. POTASSIUM iodide (21.4g, 129 mmol) dissolved in water (100 mL) was added slowly whilst the mixture was virgorously stirred. After addition, the mixture was allowed to warm to room temperature. Ethyl acetate was added and the phases were separated. The aqueous phase was extracted with ethyl acetetate (3 X). The combined organic phases were then washed with 1M NAOH, 1M Na2S203,1M HCl,- 1M saturated NAHCO3 and brine. The separated organic phase was dried (MGS04), filtered and concentrated in vacuo. The product was purified by flash chromatography using silica gel and eluting with HEPTANE/ETHYL acetate 1: 1. The product was identified from relevant fractions which were combined and concentrated IN VACUO. Yield: 24.12g, 78%

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; H. LUNDBECK A/S; WO2004/96761; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem