Category: 13726-14-2

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. 13726-14-2, name is 4-Chloro-3-methoxyaniline, A new synthetic method of this compound is introduced below., Computed Properties of C7H8ClNO

Step 1(4-Chloro-3-methoxy-phenyl)-methyl-amineIn a 50 mL flask are added 4-Chloro-3-methoxy-phenylamine (907 mg), sodium methoxide (1.56 g), 10 mL anhydrous methanol, and paraformaldehyde (690 mg). Reaction mixture is then stirred overnight at room temperature. Then, paraformaldehyde (173 mg) and sodium methoxyde (311 mg) are added, and reaction mixture is heated at reflux for 1 hour. Sodium borohydride (436 mg) is then added, and reaction mixture is stirred at reflux for 4 hours. Once back at room temperature, mixture is partially evaporated, and KOH aq 1M (50 mL) is then added. The obtained suspension is extracted by Et20, organic phase is dried over Na2S04 and evaporated. The obtained residue is purified by flash chromatography (cHex to cHex/EtOAc 8/2) to give 650 mg of the expected product (66 %).MS [M+H]+ m/z = 171.9 1H-NMR (DMSO- 6) : delta (ppm) 2.66 (d, J = 4.9 Hz, 3H) ; 3.77 (s, 3H) ; 5.80 (q, J = 4.9 Hz, 1H) ; 6.09 (dd, J = 2.5 Hz, J = 8.7 Hz, 1H) ; 6.25 (d, J = 2.4 Hz, 1H) ; 7.04 (d, J = 8.7 Hz, 1H).

The synthetic route of 13726-14-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITE DE LILLE 2 DROIT ET SANTE; INSTITUT PASTEUR DE LILLE; INSERM (INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE); CHARTON, Julie; DEPREZ, Benoit; LEROUX, Florence; STAELS, Bart; MUHR-TAILLEUX, Anne; HENNUYER, Nathalie; LESTAVEL, Sophie; LASSALLE, Manuel; DUBANCHET, Barbara; WO2015/189330; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 13726-14-2,Some common heterocyclic compound, 13726-14-2, name is 4-Chloro-3-methoxyaniline, molecular formula is C7H8ClNO, 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 substituted 2,4-dichloropyrimidine (1.0 equiv.), and substituted aniline (1.0-1.05 equiv.), and DIPEA (1.2 equiv.) in isopropanol (0.1 M) was stirred and heated at reflux. The reaction time, work-up, and product isolation procedure are described below. 2-Chloro-/Y4-(4-chloro-3-methoxyphenyl)-6-methylpyrimidin-4-amine (SG2-053-01): This was prepared from 2,4-dichloro-6-methylpyrimidine (0.326 g), 4-chloro-3-methoxyaniline (0.331 mg), and DIPEA (0.420 mL) using procedure B (reaction time, 3 d). Ethyl acetate (15 mL) was added to the mixture which was then washed with water (15 mL). The aqueous layer was re-extracted with EtOAc (15 mL). The organic layers were combined, washed with water and brine (15 mL each), dried (Na2S04), and concentrated under reduced pressure. The resulting residue was purified via column chromatography (S1O2) eluting with hexanes/EtOAc (2:8 to 3:4 v/v) to give the title compound as an off-white solid (0.334 g, 59%). Mp: 168-169 C. NMR (400 MHz, DMSO-ifc): delta 10.02 (s, 1H, disappeared on D20 shake), 7.44 (d, / = 1.7 Hz, 1H), 7.36 (d, / = 8.6 Hz, 1H), 7.17 (dd, / = 8.6, 1.7 Hz, 1H), 6.59 (s, 1H), 3.83 (s, 3H), 2.28 (s, 3H). HPLC-MS (ESI+): m/z 286.1 [70%, (M35C137C1+H)+], 284.1 [100%, (M35C135C1+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-Chloro-3-methoxyaniline, its application will become more common.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas J.; LAWRENCE, Harshani R.; (293 pag.)WO2017/66428; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 13726-14-2, A common heterocyclic compound, 13726-14-2, name is 4-Chloro-3-methoxyaniline, molecular formula is C7H8ClNO, 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: Procedure B: A mixture of substituted 2,4-dichloropyrimidine (1.0 equiv.), and substituted aniline (1.0-1.05 equiv.), and DIPEA (1.2 equiv.) in isopropanol (0.1 M) was stirred and heated at reflux. The reaction time, work-up, and product isolation procedure are described below.

The synthetic route of 13726-14-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas, J.; LAWRENCE, Harshani, R.; (257 pag.)WO2016/22460; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 13726-14-2, name is 4-Chloro-3-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Chloro-3-methoxyaniline

A stirred solution of 4-chi oro-3-methoxy-aniline (92, 5 g, 31.73 mmol) and diethyl 2- (ethoxymethylene)propanedioate (77, 10.29 g, 47.59 mmol, 9.53 mL) was heated to 100C and stirred for 2 hours and then further heated to 165 C and stirred for an additional hour. Diphenyl ether (50.0 mL) was added to the resulting solution and the reaction was heated to 280 C and stirred for 5 hours. The resulting reaction mixture was cooled to room temperature, pet ether (250 mL) was added and the reaction was stirred for 10 minutes at room temperature. The resulting solid was filtered, washed with pet ether and dried under vacuum to yield ethyl 6-chloro-4- hydroxy-7-methoxy-quinoline-3-carboxylate (93, 8.0 g, 28.40 mmol, 89.51% yield) as an off white solid. LCMS (ES+): m/z 282 [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 13726-14-2.

Reference:
Patent; C4 THERAPEUTICS, INC.; NASVESCHUK, Christopher, G.; HENDERSON, James, A.; VORA, Harit, U.; VEITS, Gesine, Kerstin; PHILIPS, Andrew, J.; (576 pag.)WO2020/51235; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 13726-14-2,Some common heterocyclic compound, 13726-14-2, name is 4-Chloro-3-methoxyaniline, molecular formula is C7H8ClNO, 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: Procedure B: A mixture of substituted 2,4-dichloropyrimidine (1.0 equiv.), and substituted aniline (1.0-1.05 equiv.), and DIPEA (1.2 equiv.) in isopropanol (0.1 M) was stirred and heated at reflux. The reaction time, work-up, and product isolation procedure are described below.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Chloro-3-methoxyaniline, its application will become more common.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas, J.; LAWRENCE, Harshani, R.; (257 pag.)WO2016/22460; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 13726-14-2, 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. 13726-14-2 name is 4-Chloro-3-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.

Concentrated hydrochloric acid (12 mL) and a solution of sodium nitrite (1.7 g, 24.4 mmol) in water (8 mL) were added to a solution of 4-chloro-3-methoxy aniline (3.86 g, 24.4 mmol) in water (8 mL), at -10 C. The mixture was stirred for 30 minutes and was then added to solution of tin chloride (14.89 g, 66 mmol) in concentrated hydrochloric acid (24 mL) and water (24 mL), cooled to 0 C. The reaction mixture was stirred for 18 hours, allowing the temperature to rise to 25 C. The resulting precipitate was filtered off and the solid was re-crystallized from heptanes/ethyl acetate (33:66) to afford the title compound the title compound as white solid in 72% yield, 3 g

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Chloro-3-methoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; Mathias, John Paul; Millan, David Simon; Lewthwaite, Russell Andrew; Phillips, Christopher; US2006/35922; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 13726-14-2, name is 4-Chloro-3-methoxyaniline, A new synthetic method of this compound is introduced below., SDS of cas: 13726-14-2

A mixture of 26 (0.25 mmol), 3-chloro-4-methoxyaniline (0.75 mmol), TEA (0.75 mmol) and NaI (0.025 mmol) in NMP (2 mL) was heated to 130 C. and stirred overnight. The mixture was diluted with AcOEt (10 mL) and washed with H2O (2¡Á10 mL). The organic layers were dried over Na2SO4, filtered and evaporated under reduce pressure. Flash Chromatography (eluent: 5% MeOH in AcOEt) gave the desired product L (10% yield). MS ESI (m/z) 407 (M+H)+.

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; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; Landry, Donald W.; Deng, Shixian; Arancio, Ottavio; Fiorito, Jole; Wasmuth, Andrew; (41 pag.)US10626113; (2020); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 13726-14-2, These common heterocyclic compound, 13726-14-2, name is 4-Chloro-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.

General procedure: Anilines (1 mmol), N,N-dimethylcarbamoyl chloride (2 mmol), DMAP (1 mmol), and pyridine (4mmol) were sequentially added under air to a reaction tube equipped with a stir bar and aseptum. CH2Cl2 (2 mL) was added by syringe and the resulting mixture vigorously stirred for36-48 h at ambient temperature. After this time, the contents of the flask were extracted withEtOAc. The solution obtained was filtered through the plug of silica gel and anhydrous MgSO4,and then concentrated by rotary evaporation. The residue was purified by flash chromatography,eluting with hexane/EtOAc to afford the product.

Statistics shows that 4-Chloro-3-methoxyaniline is playing an increasingly important role. we look forward to future research findings about 13726-14-2.

Reference:
Article; Nishikata, Takashi; Abela, Alexander R.; Huang, Shenlin; Lipshutz, Bruce H.; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 1040 – 1064;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 13726-14-2, name is 4-Chloro-3-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 13726-14-2

Ethyl 2-chloro-4-(4-chloro-3-methoxyphenylamino)pyrimidine-5-carboxylate (RJ1- 061): A mixture of ethyl 2,4-dichloropyrimidine-5-carboxylate (0.442 g, 2.0 mmol), 4-chloro-3- methoxyaniline (0.331 g, 2.1 mmol), DIPEA (0.42 mL, 2.4 mmol), and iPrOH (2 mL) was added to a 5 mL microwave vial which was then sealed and placed in a hot oil bath with stirring at 85 C overnight for 17 hours. At this point, a brown solid had formed and this was then washed with iPrOH (10 mL), water (10 mL), iPrOH (10 mL), and hexanes (10 mL) to yield RJ1-061 as a brown solid (0.570 g, 83%). m.p. = 119 C (decomposed). XH NMR (400 MHz, DMSO-) delta 10.27 (s, 1H), 8.81 (s, 1H), 7.48 (d, J= 2.3 Hz, 1H), 7.43 (d, J= 8.6 Hz, 1H), 7.28 (dd, J= 8.6, 2.3 Hz, 1H), 4.37 (q, J= 7.1 Hz, 2H), 3.85 (s, 3H), 1.34 (t, J= 7.1 Hz, 3H). LRMS (ESI+) m/z 342.1 (MC135C135+H)+, 344.0 (MC135C137+H)+, 346.0 (MC137C137+H)+; (ESI-) m/z 339.3 (MC135C135-H)-; HRMS (ESI+) m/z calculated for C14H13CI2N3O3 (M+H)+ 342.04067, found 342.04100.

According to the analysis of related databases, 13726-14-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas, J.; LAWRENCE, Harshani, R.; (257 pag.)WO2016/22460; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 13726-14-2, name is 4-Chloro-3-methoxyaniline, molecular formula is C7H8ClNO, 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. category: chlorides-buliding-blocks

General procedure: Compounds 2-19 were synthesized by reductive alkylation ofcommercially available anilines with N-Boc-2-aminoacetaldehydeand benzoylation with 2,4-dichlorobenzoyl chloride with subsequentremoval of Boc-protecting group with 4 N HCl in dioxane.Compound precipitated from hexane/ dioxane reaction mixtureas HCl salt.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13726-14-2, its application will become more common.

Reference:
Article; Buchynskyy, Andriy; Gillespie, J. Robert; Hulverson, Matthew A.; McQueen, Joshua; Creason, Sharon A.; Ranade, Ranae M.; Duster, Nicole A.; Gelb, Michael H.; Buckner, Frederick S.; Bioorganic and Medicinal Chemistry; vol. 25; 5; (2017); p. 1571 – 1584;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics