Category: 93-50-5

Electric Literature of 93-50-5, 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. 93-50-5, name is 4-Chloro-2-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 6,8-dichloro-4-oxo-chromene-2-carboxylic acid (Int-2, 1.3 g, 5.02 mmol) in DCM (20 mL) was added 4-chloro-2-methoxyaniline (949 mg, 6.02 mmol), DIPEA (1.15 g, 8.9 mmol) and HATU (3.3 g, 8.9 mmol) at room temperature and the resulting mixture was then stirred at room temperature for 18 hours. After the reaction was completed, the mixture was diluted with water (30 mL) and extracted with EtOAc (50 mL) three times. The combined organic layer was washed with brine, dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by silica gel flash chromatography (elution with PE/EtOAc=lO: 1-1:4) to give 6,8-dichloro-N-(4-chloro-2-methoxyphenyl)-4-oxo-chromene-2-carboxamide (1.6 g, 80 %) as a yellow solid. MS obsd. (ESP) [(M+H)+]: 398.1.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FENG, Song; LIANG, Chungen; LIU, Yongfu; TAN, Xuefei; WU, Jun; WANG, Jianping; (134 pag.)WO2020/79106; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 93-50-5,Some common heterocyclic compound, 93-50-5, name is 4-Chloro-2-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 solution of 4-chloro-2-methoxyaniline (4.93 g, 31.3 mmol) in THF (70 ml) was treated with BOC-anhydride (11.00 ml, 47.4 mmol) and heated at 70 overnight. LCMS showed that most of starting materials were converted to product. The solution was treated with silica gel and evaporated under reduced pressure. The material was divided into two batches, each of which was chromatographed by Biotage MPLC (50 g silica gel column, 0 to 1% EtOAc in hexanes). Like fractions from the two columns were combined and evaporated under reduced pressure to provide a clear colorless liquid. Heptane (-80 mL) was added, then evaporated under reduced pressure to provide a clear, very viscous liquid. LCMS and NMR are consistent with tert-butyl 4-chloro-2-methoxyphenylcarbamate (7.66 g, 29.7 mmol, 95 % yield). 1H NMR (300 MHz, CHLOROFORM-d): delta ppm 8.08-7.96 (m, 1 H), 7.01 (br s, 1 H), 6.92 (dd, J=8.65, 2.20 Hz, 1 H), 6.83 (d, J=2.34 Hz, 1 H), 3.87 (s, 3 H), 1.53 (s, 9 H). LCMS: m/z 202 (loss of t-Bu).

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-2-methoxyaniline, its application will become more common.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ASHWELL, Susan; CAMPBELL, Ann-Marie; CARAVELLA, Justin Andrew; DIEBOLD, R. Bruce; ERICSSON, Anna; GUSTAFSON, Gary; LANCIA, David R.; LIN, Jian; LU, Wei; WANG, Zhongguo; (141 pag.)WO2016/44782; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 93-50-5,Some common heterocyclic compound, 93-50-5, name is 4-Chloro-2-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.

Preparation 38; 3-Biphenyl-4-yl-4-(4-chloro-2-methochiyphenyl)-5-methyl-4/-/-1 ,2,4-triazole; A mixture of 2-biphenyl-4-yl-5-methyl-1 ,3,4-oxadiazole [(1g, 4.2mmol), Bioorganic & Medicinal Chemistry, 2002, 10, 1905], the product of preparation 37 (800mg, 5.04mmol) and para-toluenesulfonic acid (200mg) in xylene (2OmL) was heated at 15O0C for 10 hours. Further para-toluenesulfonic acid (100mg) was added at regular intervals, until all of the starting material was consumed. After heating at 15O0C for 4.5 hours, the reaction mixture was diluted with 2M hydrochloric acid, extracted with ethyl acetate and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with EPO dichloromethane:methanol:0.88 ammonia, 98:2:0.2. The appropriate fractions were evaporated under reduced pressure and the residue was triturated with ethyl acetate (x3) to afford the title compound as a pale brown solid in 51% yield, 860mg.1HNMR(400MHz, CDCI3) delta: 2.30(s, 3H), 3.74(s, 3H), 7.04-7.10(m, 3H), 7.32-7.57(m, 9H); LRMS APCI m/z 376 [M+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-2-methoxyaniline, its application will become more common.

Reference:
Patent; PFIZER LIMITED; WO2006/100588; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 93-50-5 as follows. COA of Formula: C7H8ClNO

Reference Example 40 4-Chloro-2-methoxy-5-nitroaniline To a suspension of 4-chloro-2-methoxyaniline (1.88 g) in concentrated sulfuric acid (18 mL) was added guanidine nitrate (1.46 g) under ice-cooling over 15 minutes, and the mixture was stirred at the same temperature for 15 minutes. The reaction mixture was poured into a saturated aqueous sodium carbonate solution cooled in ice, and the precipitated crystals were collected by filtration. The crystals were dissolved in ethyl acetate, and the solution was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (1.94 g).

According to the analysis of related databases, 93-50-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; EP2143724; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 93-50-5, name is 4-Chloro-2-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 93-50-5, category: chlorides-buliding-blocks

General procedure: Aniline (0.94 g,0.010 mol) was added dropwise, with stirring, to syrupy phosphoricacid (15 mL) at 0C. Finely ground sodiumnitrite (0.83 g,0.012 mol) was added with stirring over 15 min. This solutionwas allowed to stand at 0C for ca. 1 h after which time urea(ca. 100 mg) was added to destroy unreacted nitrite. After a further30min at 0C, a solution of freshly distilledmercaptoaceticacid (0.92 g, 0.010 mol) in water (250 mL) at 0C was addedswiftlywithvigorous stirring,maintainingapHof ca. 4. After ca.1 h of stirring at 0C, a dense pale buff precipitate had formed.The suspension was then filtered, washed with distilled waterand dried in a vacuum desiccator. A second crop of precipitatewas obtainedonkeeping the filtrate for severalhours at 0C. Thecombined dried crops were purified by dissolving in a minimumof dry diethyl ether and adding dry petroleum ether (bp. 40-60C) at 0C. After 1 h at 0C, fine, very pale buff needles wereformed; these were filtered and dried in vacuo to give 1a (1.51 g,77%).

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-2-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Buglass, Alan J.; Datta, Mrityunjoy; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 193; 4; (2018); p. 218 – 224;,
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. 93-50-5, name is 4-Chloro-2-methoxyaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 4-Chloro-2-methoxyaniline

Step A: 4-Chloro-2-iodo-6-methoxy-phenylamine To a solution of 4-chloro-2-methoxy-phenylamine (600 mg, 3.81 mmol) in ethanol (12 ml) at 50 C. was added a solution of silver sulphate (2.14 g, 6.85 mmol) and iodine (967 mg, 3.81 mmol) in ethanol (8 ml). The resulting reaction mixture was stirred at 50 C. for 4 h. After cooling at 25 C., reaction mixture was filtered through a bed of celite and the filtrate was diluted with EtOAc (30 ml). The organic phase was washed with aqueous Na2S2O3 solution (2*15 ml), and brine (10 ml), dried over anhydrous Na2SO4, filtered, and evaporated off in vacuo. The crude residue was purified by flash column chromatography (2% EtOAc in hexane) to afford 4-chloro-2-iodo-6-methoxy-phenylamine (160 mg, 15%) as brown sticky liquid. GC-MS: 283 (M).

The synthetic route of 93-50-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; Ceccarelli, Simona M.; Conte, Aurelia; Kuehne, Holger; Kuhn, Bernd; Neidhart, Werner; Obst Sander, Ulrike; Rudolph, Markus; US2013/116234; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 93-50-5, These common heterocyclic compound, 93-50-5, name is 4-Chloro-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.

Stepl[00173j To a stirred solution of Intermediate 1(0.25 g, 1.22 mmol) in DMA (3 mL) was added 4-chloro-2-methoxyaniline (0.25 g, 1.58 mmol) followed by NaHMDS (1M in THF, 3.66 mL, 3.66 mmol). The reaction was stirred for 20 minutes and then water was gradually added resulting in the product crashing out as a precipitate. The product was collected by filtration, washed with additional water and then dried under vacuum providing Intermediate 12 (361 mg, 91% yield). LC retention time 3.44 mm [A].

The synthetic route of 93-50-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MOSLIN, Ryan M.; LIN, Shuqun; WEINSTEIN, David S.; WROBLESKI, Stephen T.; ZHANG, Yanlei; TOKARSKI, John S.; WO2014/74660; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

93-50-5, name is 4-Chloro-2-methoxyaniline, belongs to chlorides-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. Application In Synthesis of 4-Chloro-2-methoxyaniline

7-Chloro-5-methoxy-2H-benzorein ,2,41thiadiazin-3(4H)-one 1 ,1 -dioxide (lnt-1) (2128) To a vigorously stirred solution of 4-chloro-2-methoxyaniline (4.8 g) in 1 -nitropropane (10 ml_) at -40 C was added chlorosulfonyl isocyanate (3.5 ml_) in 1 -nitropropane (40 ml_) dropwise. The reaction mixture was allowed to warm to 0 C and aluminum chloride (5.5 g) was added in portions. The reaction mixture was then allowed to stir at 1 10 C for 30 minutes. The reaction mixture was allowed to cool to room temperature and was then poured into ice water (250 mL) and stirred for 10 minutes. The resulting precipitate was collected by filtration, washed with water, air-dried and then dried in vacuum for 24 hours, affording the titled compound (3.6 g) as a brown solid, which was used without further purification. LCMS m/z 263.0 (M+H).

The synthetic route of 93-50-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; ATOR, Laura E.; DUFFY, Kevin J.; GRAYBILL, Todd L.; KIESOW, Terence John; LIAN, Yiqian; MOORE, Michael Lee; RALPH, Jeffrey M.; RIDGERS, Lance Howard; (370 pag.)WO2017/98421; (2017); 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. 93-50-5, name is 4-Chloro-2-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 4-Chloro-2-methoxyaniline

Example 57; 4-(4-Chloro-2-methoxy-phenyl)-3-(4-ethoxy-phenyl)-5-methyl-4H-[1,2,4]triazole; The products of preparations 4 (1g, 4. 9mmol) and 91 (926mg, 5. 88mmol) were dissolved in xylene (20ml) and the reaction mixture was heated for 10 hours at 150C. Heating was continued for 4.5 hours with portions of para-toluenesulfonic acid (100mg) added to the mixture at regular intervals until tic analysis showed all of the starting material to be consumed. The reaction mixture was then taken up into 2N hydrochloric acid and ethyl acetate and partitioned. The aqueous layer was basified with sodium hydroxide pellets and re-extracted with ethyl acetate. The combined organic phase was dried over sodium sulfate and evaporated to give a dark brown oil. Trituration with diethyl ether formed a dark brown solid that was re-crystallised from ethyl acetate to produce the title compound as a beige solid (340mg). Evaporation of the ethyl acetate gave a further residue that was purified by column chromatography on silica gel, eluting with dichloromethane : methanol : 0.88 ammonia, 98.2 : 0.2, to afford further amounts of product giving a total yield of 37% (629mg). ‘H NMR (CDCI3, 400MHz) d : 1.39 (t, 3H), 2.27 (s, 3H), 3.73 (s, 3H), 3.99 (q, 2H), 6.78 (d, 2H), 7.02-7. 06 (m, 3H), 7.31 (d, 2H). MS APCI+ m/z 344 [MH] +

According to the analysis of related databases, 93-50-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/82866; (2005); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 93-50-5, name is 4-Chloro-2-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. Computed Properties of C7H8ClNO

1.45g of 4-chloro-2-methoxyaniline was dissolved in a solution of 60 ml of water and 10 ml of concentrated sulfuric acid and cooled to below 5 C in an ice bath. Further, 634 mg of sodium nitrite was dissolved in 1 ml of water and slowly added dropwise to the reaction solution, and the mixture was stirred under ice cooling for 45 minutes, and then 1.98 g of potassium iodide aqueous solution (5 ml) was added dropwise. After stirred at room temperature for 1 hour, the mixture was extracted with EtOAc, washed with a saturated aqueous solution of sodium thiosulfate, dried over anhydrous sodium sulfate and then isolated by column chromatography (PE 100%) to obtain 2.17 g of liquid, yield 88%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 93-50-5, its application will become more common.

Reference:
Patent; Shanghai Institute of Materia Medica, Chinese Academy of Sciences; DUAN, Wenhu; GENG, Meiyu; WANG, Yuming; AI, Jing; FAN, Jun; DAI, Yang; DING, Jian; (133 pag.)EP3486244; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics