Category: 524955-09-7

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. 524955-09-7, name is 3-Chloro-4-(pyridin-2-ylmethoxy)aniline. This compound has unique chemical properties. The synthetic route is as follows. Safety of 3-Chloro-4-(pyridin-2-ylmethoxy)aniline

To a 4-Chloro-5,8-dihydro-6H-9-thia-1,3,7-triaza-fluorene-7-carboxylic acid tert-butyl ester (3.08 g, 9.40 mmol, 1.05 equiv) in 40 mL of isopropyl alcohol solution was added 3-Chloro-4-(pyridin-2-ylmethoxy)phenylamine (2.10 g, 9.0 mmol, 1 equiv) at rt. 4 N HCl in dioxane (0.1 mL) was added to the reaction mixture to accelerate the reaction. The reaction mixture was heated at 80 C. for 16 h. The mixture was allowed to cool to rt then filtered and washed with IPA (50 mL). DCM (100 mL) and sat. sodium bicarbonate (100 mL) were added to the solid. The mixture was stirred at rt for 1 h before separated the layers. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to yield 4.50 g of crude material. The crude material was purified by flash chromatography (50% THF/DCM) to yield a light yellow (3.60 g, 6.87 mmol, 76%) as product. 1H-NMR (DMSO-d6) delta 9.32 (broad s, 1H), 8.67 (d, J=4.0 Hz, 1H), 8.40 (s, 1H), 8.27 (s, 1H), 8.05 (t, 1H), 7.79 (d, J=2.7 Hz, 1H), 7.70 (d, J=8.0 Hz, 1H), 7.53 (t, 1H), 7.24 (d, J=8.9 Hz, 1H), 5.35 (s, 2H), 4.66 (s, 2H), 3.66 (t, 2H), 3.19 (t, 2H), 1.43 (s, 9H); LCMS RT=3.39 min, [M+H]+=524.0.

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, 524955-09-7, 3-Chloro-4-(pyridin-2-ylmethoxy)aniline.

Reference:
Patent; BAYER HEALTHCARE AG; US2010/298297; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 524955-09-7, 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. 524955-09-7, name is 3-Chloro-4-(pyridin-2-ylmethoxy)aniline. A new synthetic method of this compound is introduced below.

Step C: [3-chloro-4-(2-pyridylmetoxyl)-phenyl]-(6-iodo-quinazolin- 4-yl)-aminehydrochloride salt (compound 8.3).[0126] 470mg of compound 8.3 (2 mmol) and 580mg of 4-chloro-6-iodo-quinazoline (2 mmol) were dissolved in isopropanol (10 ml). The reaction mixture was refluxed for 12 hours. The solid product was collected by filtration, washed with cold isopropanol (10 mL) and ether (20 mL), and air dried to afford 450 mg of the clean desired material.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,524955-09-7, 3-Chloro-4-(pyridin-2-ylmethoxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; KANIONUSA INC.; SHEN, Wang; ZHANG, Aimin; FAN, Junfa; ZHENG, Xiaoling; WO2011/2523; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 524955-09-7, 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. 524955-09-7, name is 3-Chloro-4-(pyridin-2-ylmethoxy)aniline, molecular formula is C12H11ClN2O, The 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.

Following hydrogenation to form the first aniline intermediate, acid catalyzed coupling was performed to prepare 4-[3-chloro-4-(2-pyridylmethoxy)anilino]-3-cyano-7-ethoxy-6-N-acetylaminoquinoline, as shown below: To perform the coupling reaction, the two reactants were heated together in alcohol at 65-78 C. over 4-6 hours, yielding the product. The reaction begins as an amber slurry and thickens to a lighter beige slurry as it approaches completion. Upon scaling up from 75 g to 350 g, it proved necessary to add a catalytic amount (0.025 eq.) of methanesulfonic acid to initiate the reaction. As a specific example, 4-chloro-3-cyano-7-ethoxy-6-N-acetylaminoquinoline (0.141 kg, 0.49 mole) was added to the mixture of Example 2, followed by ethanol (0.037 L) to give a suspension. A catalytic amount of methanesulfonic acid (1.17 g) was added at 20-25 C. The resulting slurry was heated to 70-75 C. and held for a minimum of 4 hours. Thickening of the slurry was evident after 1.5 hours. Following reaction completion, the mixture was cooled to room temperature and may be used ?as is? in the telescoped reaction of Example 4 below.; As solvents EtOH, DMF or other suitable solvent may be used. Experimental results obtained using different solvents and reaction conditions are shown in Table 3. Difficulty filtering the product of this step (noted in several entries on Table 3) was circumvented by not isolating the solid at this point, but telescoping the reaction with the next step. It has been found that on the order of 20 volumes of EtOH were necessary to achieve reasonable stirring, but that the reaction can proceed in only 10 volumes of DMF, without significant loss in purity. In Table 3, where the entry is labelled NI, the intermediate product was not isolated, but carried into the next reaction step. TABLE 3 Coupling Reaction Coupling Temp Time Yield Solvent Solvent ( C.) (h) (%) Comments IPA EtOH 78 4 85.4 contains impurity THF EtOH 78 4 90.5 v. slow filtration THF THF 68 4 NA Only 16% product formed THF EtOH 78 4 94.2 v. slow filtration EtOH IPA 82 5 NA No reaction EtOH MeOH 65 5 60.0 v. slow filtration THF EtOH 78 1.5 80.3 v. slow filtration (MeSO3H) THF EtOH 78 4 86.0 v. slow filtration THF EtOH 78 3 85.7 4 h filtration – hard, green (MeSO3H) coated solid on drying THF Dimethoxy 85 2 74.2 Faster filtration (<1 hr) ethane Nice yellow solid THF Diethoxy 85 5 - - Methane THF Dimethoxy 70 6 - - Ethane THF EtOH 78 6 96.6 Slow filtration THF DMF 78 0.5 65.6 Some product lost in filtrate (MeSO3H) THF DMF 70 8 NI See Note 1 (MeSO3H) THF EtOH 78 6 ND See Note 2 (MeSO3H) THF EtOH 78 4 NI Yield to the free base is (MeSO3H) 80.4%3/ THF EtOH 75 4 NI Yield to the free base is (MeSO3H) 83%3/ THF EtOH 75 4 NI Yield to the free base is (MeSO3H) 86%3/ NR = no reaction, NI = not isolated; ND = not determined; NA = not available 1. Carried through to the deprotection and generation of free base to give 69.5% overall yield. 2. The overall yield after the deprotection and generation of the free base is 76.1% 3This reaction was not filtered at all but taken as slurry to the next step. While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 524955-09-7, 3-Chloro-4-(pyridin-2-ylmethoxy)aniline. Reference:
Patent; WYETH; US2006/270668; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 524955-09-7, 3-Chloro-4-(pyridin-2-ylmethoxy)aniline, 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, 524955-09-7, blongs to pyridine-derivatives compound. Application In Synthesis of 3-Chloro-4-(pyridin-2-ylmethoxy)aniline

A mixture of N-(4-chloro-3-cyano-7-(2-methoxyethoxy)quinolin-6-yl)acetamide (6.3g, 0.0197 mol, 1.00 equiv), 3-chloro-4-(2-pyridylmethoxy)aniline (4.7g, 0.0201mol, 1.00 equiv), methanesulfonic acid (0.7ml, 0.0108 mol) and ethanol (150 ml) was stirred under refluxed for 6 hours and then 0.6N hydrogen chloride (300 ml, 0.18 mol) was added. The mixture was heated to 80 0C for 19 hours, and then cooled to 0 0C to form precipitate. The precipitated solids were filtered and then added to a solution of IN potassium carbonate (100ml, O.lmol) in methanol (150ml) and then the mixture was stirred for 3 hours. The resulting mixture was filtered, washed with 1 : 1 methano I/water (300ml) and dried to give product 6.4g. MS (ESI) m/z: 475 (M+l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,524955-09-7, its application will become more common.

Reference:
Patent; MEDOLUTION LIMITED; ZHANG, Dawei; WO2010/151710; (2010); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 524955-09-7, 3-Chloro-4-(pyridin-2-ylmethoxy)aniline, 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, 524955-09-7, blongs to pyridine-derivatives compound. Application In Synthesis of 3-Chloro-4-(pyridin-2-ylmethoxy)aniline

A mixture of N-(4-chloro-3-cyano-7-(2-methoxyethoxy)quinolin-6-yl)acetamide (6.3g, 0.0197 mol, 1.00 equiv), 3-chloro-4-(2-pyridylmethoxy)aniline (4.7g, 0.0201mol, 1.00 equiv), methanesulfonic acid (0.7ml, 0.0108 mol) and ethanol (150 ml) was stirred under refluxed for 6 hours and then 0.6N hydrogen chloride (300 ml, 0.18 mol) was added. The mixture was heated to 80 0C for 19 hours, and then cooled to 0 0C to form precipitate. The precipitated solids were filtered and then added to a solution of IN potassium carbonate (100ml, O.lmol) in methanol (150ml) and then the mixture was stirred for 3 hours. The resulting mixture was filtered, washed with 1 : 1 methano I/water (300ml) and dried to give product 6.4g. MS (ESI) m/z: 475 (M+l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,524955-09-7, its application will become more common.

Reference:
Patent; MEDOLUTION LIMITED; ZHANG, Dawei; WO2010/151710; (2010); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 524955-09-7, Adding some certain compound to certain chemical reactions, such as: 524955-09-7, name is 3-Chloro-4-(pyridin-2-ylmethoxy)aniline,molecular formula is C12H11ClN2O, 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 524955-09-7.

General procedure: A mixture of (E)-N’-(2-cyano-4-nitrophenyl)-N,N-dimethylformimidamide (5) (2.99g, 13.7 mmol) and appropriate aniline (15.1 mmol) in glacial acetic acid (15.0mL) was refluxed for 2 h. The acetic acid was evaporated and the solid waswashed with water and diethyl ether and dried to afford the titled compounds.

According to the analysis of related databases, 524955-09-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Elkamhawy, Ahmed; Farag, Ahmed Karam; Viswanath, Ambily Nath Indu; Bedair, Tarek M.; Leem, Dong Gyu; Lee, Kyung-Tae; Pae, Ae Nim; Roh, Eun Joo; Bioorganic and Medicinal Chemistry Letters; vol. 25; 22; (2015); p. 5147 – 5154;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 524955-09-7, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 524955-09-7, name is 3-Chloro-4-(pyridin-2-ylmethoxy)aniline. This compound has unique chemical properties. The synthetic route is as follows.

0.500 g (2.14 mmol) of 3-chloro-4-(pyridin-2-ylmethoxy)aniline, 0.317 g (2.14 mmol) of 2,4-dichloropyrimidine, 0.499 g (4.28 mmol)Triethylamine and 5 mL of ethanol were added to the reaction flask and refluxed at 79 C for 6 h.After the reaction, it was cooled to room temperature. The solvent was removed by steaming under reduced pressure.Add 10mL of water,Extract with ethyl acetate (3 x 15 mL) and combine the organic phases.The organic phase is dried over anhydrous sodium sulfate and concentrated.Separated by silica gel column chromatography (dichloromethane: ethyl acetate = 1:20, V/V).Obtained as a pale yellow solid 2-(3-chloro-4-(pyridin-2-ylmethoxy)phenylamino)-4-chloropyrimidine0.496 g, the yield is 67%.

According to the analysis of related databases, 524955-09-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shaanxi Normal University; Li Baolin; Hao Yunxia; Zhang Yaling; Li Xiabing; Wang Wei; (22 pag.)CN109516959; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 524955-09-7, 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. 524955-09-7, name is 3-Chloro-4-(pyridin-2-ylmethoxy)aniline. A new synthetic method of this compound is introduced below.

Following hydrogenation to form the first aniline intermediate, acid catalyzed coupling was performed to prepare 4-[3-chloro-4-(2-pyridylmethoxy)anilino]-3-cyano-7-ethoxy-6-N-acetylaminoquinoline, as shown below: To perform the coupling reaction, the two reactants were heated together in alcohol at 65-78 C. over 4-6 hours, yielding the product. The reaction begins as an amber slurry and thickens to a lighter beige slurry as it approaches completion. Upon scaling up from 75 g to 350 g, it proved necessary to add a catalytic amount (0.025 eq.) of methanesulfonic acid to initiate the reaction. As a specific example, 4-chloro-3-cyano-7-ethoxy-6-N-acetylaminoquinoline (0.141 kg, 0.49 mole) was added to the mixture of Example 2, followed by ethanol (0.037 L) to give a suspension. A catalytic amount of methanesulfonic acid (1.17 g) was added at 20-25 C. The resulting slurry was heated to 70-75 C. and held for a minimum of 4 hours. Thickening of the slurry was evident after 1.5 hours. Following reaction completion, the mixture was cooled to room temperature and may be used ?as is? in the telescoped reaction of Example 4 below.; As solvents EtOH, DMF or other suitable solvent may be used. Experimental results obtained using different solvents and reaction conditions are shown in Table 3. Difficulty filtering the product of this step (noted in several entries on Table 3) was circumvented by not isolating the solid at this point, but telescoping the reaction with the next step. It has been found that on the order of 20 volumes of EtOH were necessary to achieve reasonable stirring, but that the reaction can proceed in only 10 volumes of DMF, without significant loss in purity. In Table 3, where the entry is labelled NI, the intermediate product was not isolated, but carried into the next reaction step. TABLE 3 Coupling Reaction Coupling Temp Time Yield Solvent Solvent ( C.) (h) (%) Comments IPA EtOH 78 4 85.4 contains impurity THF EtOH 78 4 90.5 v. slow filtration THF THF 68 4 NA Only 16% product formed THF EtOH 78 4 94.2 v. slow filtration EtOH IPA 82 5 NA No reaction EtOH MeOH 65 5 60.0 v. slow filtration THF EtOH 78 1.5 80.3 v. slow filtration (MeSO3H) THF EtOH 78 4 86.0 v. slow filtration THF EtOH 78 3 85.7 4 h filtration – hard, green (MeSO3H) coated solid on drying THF Dimethoxy 85 2 74.2 Faster filtration (<1 hr) ethane Nice yellow solid THF Diethoxy 85 5 - - Methane THF Dimethoxy 70 6 - - Ethane THF EtOH 78 6 96.6 Slow filtration THF DMF 78 0.5 65.6 Some product lost in filtrate (MeSO3H) THF DMF 70 8 NI See Note 1 (MeSO3H) THF EtOH 78 6 ND See Note 2 (MeSO3H) THF EtOH 78 4 NI Yield to the free base is (MeSO3H) 80.4%3/ THF EtOH 75 4 NI Yield to the free base is (MeSO3H) 83%3/ THF EtOH 75 4 NI Yield to the free base is (MeSO3H) 86%3/ NR = no reaction, NI = not isolated; ND = not determined; NA = not available 1. Carried through to the deprotection and generation of free base to give 69.5% overall yield. 2. The overall yield after the deprotection and generation of the free base is 76.1% 3This reaction was not filtered at all but taken as slurry to the next step. At the same time, in my other blogs, there are other synthetic methods of this type of compound,524955-09-7, 3-Chloro-4-(pyridin-2-ylmethoxy)aniline, and friends who are interested can also refer to it. Reference:
Patent; WYETH; US2006/270668; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 524955-09-7, 3-Chloro-4-(pyridin-2-ylmethoxy)aniline, 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, Quality Control of 3-Chloro-4-(pyridin-2-ylmethoxy)aniline, blongs to pyridine-derivatives compound. Quality Control of 3-Chloro-4-(pyridin-2-ylmethoxy)aniline

Example 74 Production of N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-6-(2-furyl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine A mixture of 4-chloro-6-(2-furyl)-5H-pyrrolo[3,2-d] pyrimidine (80 mg), 3-chloro-4- (pyridin-2-ylmethoxy) aniline (94 mg) and 1-methyl-2-pyrrolidinone (2.5 mL) was stirred at 140C for 2 hrs, poured into water (10 mL) and adjusted to pH 8 with saturated aqueous sodium hydrogen carbonate. The mixture was extracted with ethyl acetate (30 mLx2). The organic layers were combined and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=1:1 ? 0:1). The object fraction was concentrated under reduced pressure. Chloroform – diisopropyl ether was added to the residue, and the solid was collected by filtration and dried under reduced pressure at 60C to give the title compound (71 mg). 1H-NMR (DMSO-d6) delta 5.27 (2H, s), 6.72 (1H, m), 6.78 (1H, d, J= 1.2 Hz), 7.02 (1H, d, J= 3.3 Hz), 7.26 (1H, d, J= 9.0 Hz), 7.36 (1H, m), 7.53-7.59 (2H, m), 7.81 (1H, d, J= 8.1 Hz), 7.91 (1H, s), 8.21 (1H, d, J= 2.4 Hz), 8.34 (1H, s), 8.59 (1H, d, J= 5.1 Hz), 9.19 (1H, br s), 11.62 (1H, br s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,524955-09-7, 3-Chloro-4-(pyridin-2-ylmethoxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1752457; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 524955-09-7, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 524955-09-7, name is 3-Chloro-4-(pyridin-2-ylmethoxy)aniline. This compound has unique chemical properties. The synthetic route is as follows.

Compound 40 (0.66 g, 2.56 mmol), 26 (0.6 g, 2.56 mmol) and pyridine hydrochloride (0.3 g, 2.56 mmol) were added to DME (15 mL) and the solution was heated to reflux for 5 h. The reaction mixture was diluted with water (100 mL) and the resulting solid was filtered, washed with water and dried to give 4-((3-chloro-4-(pyridin-2-ylmethoxy)phenyl)amino)-5-(4-nitrophenyl)nicotinonitrile 43a (0.88 g, 75%) as a faint-yellow solid. MS-ESI (m/z): 458.4(M+H), 480.3(M+Na); 1H NMR (DMSO-d6, delta): 5.19(d, 2H), 6.99-7.08(m, 2H), 7.18(s, 1H), 7.37(m, 1H), 7.47(d, 1H), 7.67(d, 2H), 7.85(t, 1H), 8.21(d, 2H), 8.34(s, 1H), 8.57(d, 1H), 8.66(s, 1H), 8.72(s, 1H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 524955-09-7, 3-Chloro-4-(pyridin-2-ylmethoxy)aniline.

Reference:
Article; Mao, Yongjun; Zhu, Wenxiu; Kong, Xiaoguang; Wang, Zhen; Xie, Hua; Ding, Jian; Terrett, Nicholas Kenneth; Shen, Jingkang; Bioorganic and Medicinal Chemistry; vol. 21; 11; (2013); p. 3090 – 3104;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem