Category: 19056-40-7

19056-40-7, 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 19056-40-7 as follows.

To a solution of ethyl (2Z)-3-(methylamino)-3-phenylacrylate (4.47 g, 21.77 mmol) in DCM (100 mL) was added 4-bromo-3-methoxyaniline (4 g, 19.80 mmol) and PPTS (5.47 g, 21.77 mmol). The mixture was then heated to reflux for 24h. At this time crude IH NMR revealed nearly complete consumption of the aniline. The reaction was then cooled to r.t.,fltered, and the solvent was removed in vacuo. The crude product was purified on silica (75percent DCM/hexanes) to yield ethyl (2Z)-3- [(4-bromo-3-methoxyphenyl)amino]-3-phenylacrylate (6.5 g, 87percent) which was used as is in subsequent reactions. 1H NMR (500 MHz, CDCl3) ppm: 10.32 (br s, IH), 7.32 (m, 5H), 7.20 (d, J = 8.5 Hz, IH), 6.19 (dd, J = 8.5 Hz, 2.5 Hz, IH), 6.11 (d, J = 2.5 z, IH), 5.03 (s, IH), 4.21 (q, J = 7.0 Hz, 2H), 3.50 (s, 3H), 1.32 (t, J = 7.0 Hz, 3H).

According to the analysis of related databases, 4-Bromo-3-methoxyaniline, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2006/119061; (2006); A2;,
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19056-40-7, The chemical industry reduces the impact on the environment during synthesis 19056-40-7, name is 4-Bromo-3-methoxyaniline, I believe this compound will play a more active role in future production and life.

To a stirred solution of 4-bromo-3-methoxyaniline (0.5 g, 2.47 mmol) in toluene (5 mL) were added ethylacetoacetate (0.5 mL, 3.71), sodium ethoxide (0.34 g, 4.94 mmol), and heated to110¡ãC for 16 h. After completion of the reaction, the reaction mixture was diluted with EtOAC(100 mL), washed with water (100 mL), brine (100 mL), dried over sodium sulphate andconcentrated. The residue was purified by colunm chromatography by using silica gel (60-120mesh) to afford the title product as yellow solid (0.4 g, 90percent). 1H NMR (400 MHz, DMSO-d6): oe10.21 (s, 1H), 7.48?7.43 (m, 2H), 7.11?7.08 (m, 1H), 3.83 (s, 3H), 3.54 (s, 2H), 2.20 (s, 3H); ES-MS: mlz 286.1 (M-i-1).

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-3-methoxyaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; SAMAJDAR, Susanta; ABBINENI, Chandrasekhar; SASMAL, Sanjita; HOSAHALLI, Subramanya; WO2015/104653; (2015); A1;,
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19056-40-7, These common heterocyclic compound, 19056-40-7, name is 4-Bromo-3-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.

Under an atmosphere of nitrogen, in a 100 mL round-bottomed flask at 0¡ã C., 4-bromo-3-methoxyaniline (2 g, 9.9 mmol) and KOH (6.93 ml, 13.9 mmol) were combined with dichloromethane (30 ml) to give a light brown solution. Then 4-bromobutanoyl chloride (1.84 g, 1.15 ml, 9.9 mmol) was added. The reaction was stirred for 1 h at RT. The reaction mixture was poured into 50 ml dichloromethane and extracted with water (3*20 ml). The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in 30 ml dichloromethane. Then tetrabutylammonium bromide (63.8 mg, 198 mumol) and KOH (50percent, 6 ml) were added. The reaction was stirred for 1 h at RT. The reaction mixture was poured into dichloromethane (50 ml) and extracted with water (3*20 ml). The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 50 g, 20percent to 50percent EtOAc in heptane). The title compound was obtained as a off-white crystalline (1.92 g, 71.8percent). MS (m/e)=272.1 [M+H]+.

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 19056-40-7.

Reference:
Patent; Hoffmann-La Roche Inc.; Jakob-Roetne, Roland; Wichmann, Juergen; Peters, Jens-Uwe; Jagasia, Ravi; (33 pag.)US2016/326150; (2016); A1;,
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19056-40-7, name is 4-Bromo-3-methoxyaniline, belongs to ethers-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. 19056-40-7

Step 1. 5-({[4-bromo-3-(methyloxy)phenyl]amino}methylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione: 2,2-dimethyl-1,3-dioxane-4,6-dione (8.5 g, 58 mmol) in trimethyl orthoformate (50 mL, 450 mmol) was refluxed at 105 C for 1 hr. 4-Bromo-3-methoxyaniline (10.5 g, 50.4 mmol) was then added and refluxing was continued for and additional hour. The suspension was filtered, and the solid was washed with MeOH and vacuum dried to yield 5-({[4-bromo-3-(methyloxy)phenyl]amino}methylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (17 g, 49 mmol, 96 % yield). 1H NMR (400 MHz, DMSO-d) delta ppm 1.68 (s, 6H), 3.90 (s, 3H), 7.11 (dd, J = 8.6 Hz, 2 Hz, 1H), 7.43 (d, J= 2 Hz, 1H), 7.59 (d, J= 8.6 Hz, 1H), 8.64 (s, 1H), 11.23 (br. s., 1H).

Statistics shows that 19056-40-7 is playing an increasingly important role. we look forward to future research findings about 4-Bromo-3-methoxyaniline.

Reference:
Patent; GlaxoSmithKline Intellectual Property Development Limited; BURY, Michael, Jonathan; CASILLAS, Linda, N.; CHARNLEY, Adam, Kenneth; HAILE, Pamela, A.; MARQUIS, Robert, W., Jr.; MEHLMANN, John, F.; ROMANO, Joseph, J.; SINGHAUS, Robert, R.; WANG, Gren, Z.; (83 pag.)EP2680844; (2016); B1;,
Ether – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 19056-40-7, name is 4-Bromo-3-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 19056-40-7, 19056-40-7

2,2-Dimethyl-1,3-dioxane-4,6-dione (8.5 g, 58 mmol) in trimethyl orthoformate (50 mL, 450mmol) was refluxed at 105C for 1 hr. 4-Bromo-3-methoxyaniline (commercially available from, for example, Aldrich) (10.5 g, 50.4 mmol) was then added and refluxing was continued for an additional hour. The suspension was filtered, and the solid was washed with methanol and vacuum dried to yield the title compound (17.0 g, 49 mmol, 96 % yield). LCMSRT= 1.10mm, ES-i-ye 356,358

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-3-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; HARLING, John David; SMITH, Ian Edward David; (79 pag.)WO2016/169989; (2016); A1;,
Ether – Wikipedia,
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Adding some certain compound to certain chemical reactions, such as: 19056-40-7, name is 4-Bromo-3-methoxyaniline, 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 19056-40-7. 19056-40-7

Method 12 2-[(4-Bromo-3-methoxyphenyl)diazenyl]-2-cyanoacetamide. Sodium nitrite (8.54 g, 123.7 mmol) dissolved in water (100 ml) was added to an ice- cold suspension of 4-bromo-3-methoxyaniline (25 g, 123.7 mmol) in concentrated HCl (46 ml, 1514 mmol) and water (100 ml). After stirring for 10 minutes, 2-cyanoacetamide (10.40 g, 123.7 mmol) and sodium acetate trihydrate (84 g, 617 mmol) in water (1.8 L) was added and the reaction was allowed to stir overnight. The resulting solid was collected by filtration, washed with water, dried, giving an orange solid which was refluxed in 1.4 L of ethanol for 30 min. The mixture was cooled to room temperature, the solid was collected by filtration, washed with ethanol (100 ml x 3), and dried to yield the title compound as a yellow solid (34.4 g, 94 percent). 1H NMR: 11.70 (s, 1 H), 7.90 (s, 1 H), 7.50 (m, 2 H), 7.35 (s, 1 H), 7.20 (d, 1 H), 3.90 (s, 3 H); m/z: 296.

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 4-Bromo-3-methoxyaniline.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/90353; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 19056-40-7 as follows. 19056-40-7

Example A5; a) Preparation of intermediate compound 7; A solution of methyl chloroglyoxalate (0.0593 mol) in CH2Cl2 (50 ml) was added por- tionwise to a mixture of 4-bromo-3-methoxybenzenamine (0.0494 mol) and Et3N (0.0741 mol) in CH2Cl2 (50 ml), stirred at 0 0C. The resultant reaction mixture was stirred for 24 hours at room temperature. A saturated aqueous NaHCO3 solution was added. The organic layer was separated, dried (Na2SO4), filtered and the solvent was evaporated. The residue was treated with diethyl ether, subsequently filtered off and dried. Yield: 12.8 g of intermediate compound 7 (91 percent).

According to the analysis of related databases, 19056-40-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2007/71646; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

A common compound: 19056-40-7, name is 4-Bromo-3-methoxyaniline, belongs to ethers-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. 19056-40-7

POCl3 (5.07 mL, 54.4 mmol) was added to a mixture of 4-bromo-3- methoxyaniline (10 g, 49.5 mmol) and malonic acid (5.15 g, 49.5 mmol) with thorough mixing, and the mixture was then heated to 105¡ãC. After 5 minutes, the reaction began to bubble vigorously, and eventually formed a hard foam; heating was continued for 1 hour. After cooling, water (200 mL) was added, and the mixture was stirred for 30 minutes. The solid was filtered off and washed with water. 2N NaOH (300 mL) was added to the solid, and stirring was continued overnight. The remaining solid was filtered off; EtOH (5 mL) was then added to the filtrate; and the basic layer was then acidified with concentrated HCl to pH 2. The resulting solid was then filtered off, washed with water. The solid was then transferred to a flask, and the remaining water was removed by stripping off EtOH (200 mL x 2). The solid was then further dried under high vacuum for 15 hours to yield 8.75 g (66percent) of the title compound as an off- white solid. LRMS ESI+ (M+H)+ 270.2/272.2.

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, 19056-40-7, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; WO2008/51514; (2008); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem