Category: 13726-14-2

Application of 13726-14-2, The chemical industry reduces the impact on the environment during synthesis 13726-14-2, name is 4-Chloro-3-methoxyaniline, I believe this compound will play a more active role in future production and life.

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.

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

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

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., Application In Synthesis of 4-Chloro-3-methoxyaniline

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

Synthetic Route 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

Electric Literature of 13726-14-2, 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.

General procedure: N-Benzylpiperidone (1 g, 5.2 mmol, 1 equiv), 3, 4 difluoroaniline (0.52 mL, 5.2 mmol, 1 equiv) and sodium sulfate (3.7 g, 26.4 mmol, 5 equiv) were suspended in dichloromethane (20 mL). Sodium triacetoxyborohydride (1.3 g, 6.33 mmol, 1.2 equiv) was added and the reaction mixture was stirred at room temperature overnight. Aqueous sodium hydrogen carbonate was added followed by stirring for 30 min. The reaction mixture was extracted with dichloromethane and the combined organic phases were washed with brine, dried over sodium sulfate, filtrated and concentrated in vacuo. The residue obtained upon evaporation of solvent was chromatographed over silica gel and eluted with 35% ethyl acetate/hexane to give the 26 as a light yellow colored solid (1.2 g, 75% yield).

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

Reference:
Article; Deekonda, Srinivas; Wugalter, Lauren; Kulkarni, Vinod; Rankin, David; Largent-Milnes, Tally M.; Davis, Peg; Bassirirad, Neemah M.; Lai, Josephine; Vanderah, Todd W.; Porreca, Frank; Hruby, Victor J.; Bioorganic and Medicinal Chemistry; vol. 23; 18; (2015); p. 6185 – 6194;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 13726-14-2, name is 4-Chloro-3-methoxyaniline, belongs to chlorides-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 13726-14-2, Quality Control of 4-Chloro-3-methoxyaniline

General procedure: The mixture of aniline 1 (1.2 mmol), alcohol (0.4 mmol), and ReH7(PCy3)2 (10 mol %,18 mg) were added into the flask. Then, anisole (0.5 mL) was added. The flask was evacuated and backfilled with CO (1.5 atm). The reaction mixture was vigorously stirred at 150 oC under for 20-36 h. After the reaction finished, the reaction mixture was cooled to room temperature and extracted with ethyl acetate (3 × 5 mL), the combined organic phases were dried over anhydrous Na2SO4 and the solvent was evaporated under vacuum. After removing the solvents in vacuum, the residue was purified by flash column chromatography on silica gel or preparative TLC on GF254to afford the desired amination products.

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:
Article; Abdukader, Ablimit; Jin, Hongming; Cheng, Yixiang; Zhu, Chengjian; Tetrahedron Letters; vol. 55; 30; (2014); p. 4172 – 4174;,
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., Formula: C7H8ClNO

A mixture of 4-chloro-6-(tetrahydro-2H-pyran-4-ylthio)quinoline (1.4 g, 5.00 mmol), 4-chloro-3-(methyloxy)aniline (0.789 g, 5.00 mmol) and ethanol (16.68 ml) was treated with concentrated HCl (1 drop) and at 80 C for 3d. The reaction was cooled to rt, poured into diethylether (300 mL) and filtered to provide crude product (1g). The material was partitioned between ethyl acetate and sat. sodium bicarbonate. The aqueous layer was extracted with ethyl acetate (1x) and the combined organic extracts were washed with brine (1x), dried over magnesium sulfate, dry-loaded onto silica gel and purified via column chromatography (ISCO-Rf, 40g column, 0-10% methanol/DCM) to afford N-[4-chloro-3-(methyloxy)phenyl]-6-(tetrahydro-2H-pyran-4-ylthio)-4-quinolinamine (700 mg, 1.746 mmol, 34.9 % yield) as a brown oil. 1H NMR (400 MHz, DMSO-d6) delta ppm 9.07 (s, 1 H), 8.48 (d, J=5.3 Hz, 1 H), 8.41 (d, J=1.8 Hz, 1 H), 7.85 (d, J=8.8 Hz, 1 H), 7.70 – 7.79 (m, 1 H), 7.43 (d, J=8.6 Hz, 1 H), 7.12 (d, J=2.3 Hz, 1 H), 7.06 (d, J=5.3 Hz, 1 H), 6.96 (dd, J=8.5, 2.4 Hz, 1 H), 3.81 – 3.90 (m, 5 H), 3.63 – 3.67 (m, 1 H), 3.40 (td, J=11.2, 2.4 Hz, 2 H), 1.84 – 1.94 (m, 2 H), 1.48 – 1.62 (m, 2 H). MS (m/z) 401(M+H)+.

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; GlaxoSmithKline Intellectual Property Development Limited; BURY, Michael, Jonathan; CASILLAS, Linda, N.; CHARNLEY, Adam, Kenneth; DEMARTINO, Michael, P.; DONG, Xiaoyang; HAILE, Pamela, A.; HARRIS, Philip, Anthony; LAKDAWALA SHAH, Ami; KING, Bryan, W.; MARQUIS, Robert, W., Jr.; MEHLMANN, John, F.; ROMANO, Joseph, J.; SEHON, Clark, A.; EIDAM, Patric; EP2566477; (2015); B1;,
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.

Step 3: Preparation of N-(4-Chloro-3-methoxyphenyl)-l-(4-methoxybenzyl)-lH- yrazolof 4, 3-b]pyridin-3-amine (Exp- 1 -g4)[0088] Into a vessel containing 1.5 mL dioxane was placed 63 mg of the crude Exp-1- g3 prepared in Step 2 (0.2 mmol). To the vessel was added 39 mg of 4-chloro-3- methoxy-phenylamine (0.25 mmol), 18 mg Pd2dba3 (0.02 mmol), 23 mg Xantphos (0.04 mmol) and 130 mg Cs2C03 (0.4 mmol). The reaction mixture thus provided was refluxed under a nitrogen atmosphere for 4 hours, then filtered and concentrated under reduced pressure. The residue was subjected to Prep-TLC (PE:EtOAc = 2: 1) to obtain Exp-l-g4 (52 mg, 66 %).

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; MERCK SHARP & DOHME CORP; ADDEX PHARMA S.A.; LIVERTON, Nigel; JONES, Philip; BOLEA, Christelle; CELANIRE, Sylvain; TANG, Lam; BOUDOU, Cedric; LEI, Zhiyu; LIU, Fuqing; LUO, Yunfu; DONG, Jingchao; SOLL, Richard; WO2013/60029; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route 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.

A solution of 4-chloro-3-methoxy-aniline (7.00 g, 44.4 mmol) dissolved in dichloromethane (100 mL) at 5 C was treated portions with NBS (8.14 g, 45.7 mmol) over 1 hour, then warmed to 20 C and stirred at 20 C for 2 hours. On completion, a 5% aqueous Na2SO3 solution (100 mL) was added and the mixture was stirred for 10 minutes. The layers were separated and the organic layer was washed with water and saturated brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The getting residue was purified by column chromatography (petroleum ether: ethyl acetate = 3:1) to give the title compound (9.00 g, 85% yield) as a dark brown solid.1H NMR (400MHz, CD3Cl) delta = 7.37 (s, 1H), 6.35 (s, 1H), 4.13 (br. s., 2H), 3.83 (s, 3H).

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; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; (215 pag.)WO2018/106636; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 13726-14-2, 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. 13726-14-2, name is 4-Chloro-3-methoxyaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 2 (100 mg, 0.411 mmol), aniline (154 mg, 0.411 mmol) and DIPEA (0.15 mL, 0.822 mmol) in n-butanol (20 mL) were added, and the mixture was stirred at 110 C for 12 h. After cooling to room temperature, the reaction mixture was concentrated. The residue was purified by silica gel chromatography using a polarity mobile phase (acetone/dichloromethane, 10:100) to give product 3a.

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

Reference:
Article; Bertrand, Jeanluc; Castro, Alejandro; Dostalova, Hana; Espinosa-Bustos, Christian; Jorda, Radek; Krystof, Vladimir; Maria Zarate, Ana; Mella, Jaime; Salas, Cristian O.; Bioorganic Chemistry; (2019);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics