Category: 2106-04-9

Some common heterocyclic compound, 2106-04-9, name is 3-Chloro-2-fluoroaniline, molecular formula is C6H5ClFN, 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. Quality Control of 3-Chloro-2-fluoroaniline

A round bottom flask was charged with 1 eq of 3-chloro-2-fluoroaniline (3A), l-methyl-2-pyrrolidinone (about 1.5 M 3A in NMP), 2.2 eq of sodium cyanide, and 1.35 eq of nickel() bromide at RT under N2. The concentration was halved by die introduction of additional NMP under N2 and the solution was gently warmed to 200+/- 5C and stirred for 4 days under N2. The reaction mixture was allowed to cool to room temperature. The reaction mixture was diluted with 30 volumes of teft-hutyl methyl ether (MTBE) and filtered through celite. The celite pad was then rinsed with 10 volumes of MTBE. The organics were washed with 40 volumes of brine, 2 x 40 volumes of water and 40 volumes of brine. The combined organics were dried over sodium sulfate and concentrated to afford a brown solid, which was dried under vacuum (~30 in Hg) at 400C for 8 hours to afford the compound of Formula 3B (71% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2106-04-9, its application will become more common.

Reference:
Patent; CYTOKINETICS, INC.; WO2007/70683; (2007); A2;,
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. 2106-04-9, name is 3-Chloro-2-fluoroaniline, A new synthetic method of this compound is introduced below., name: 3-Chloro-2-fluoroaniline

EXAMPLE 12(trans)-9-[4-(3-chloro-2-fluoro-phenylamino)-7-methoxy-quinazolin-6-yloxy]-1,4-diaza-spiro[5.5]undecan-5-one Process Step O12 g of the impure (trans)-9-(4-chloro-7-methoxy-quinazolin-6-yloxy)-1,4-diaza-spiro[5.5]undecan-5-one hydrochloride from the previous step are added batchwise to a solution of 3.9 g of 3-chloro-2-fluoroaniline in 60 ml of 2N hydrochloric acid at RT within 90 min. The suspension is heated to 40 C. for 60 min. Then 60 ml of toluene are added and the mixture is cooled to RT. After 50 min it is filtered and the precipitate is washed with 50 ml of toluene and 50 ml of sat. NaCl solution. After drying at 40 C., 10 g of a solid are obtained, which contains the product. The product is purified by basic chromatography on silica gel.Mass spectrum (ESI+): m/z=486 [M+H]+ 1H NMR (400 MHz, DMSO): 9.60 (1H, s); 8.37 (1H, s); 7.82 (1H, s); 7.45-7.54 (2H, m), 7.36 (1H, s); 7.28 (dt, 1H); 7.22 (1H, s); 4.63-4.67 (1H, m); 3.95 (3H, s); 3.11-3.15 (2H, m); 2.82-2.86 (2H, m); 2.30 (1H, s); 2.13-2.22 (2H, m); 1.83-1.96 (4H, m); 1.44-1.51 (2H, m).

The synthetic route of 2106-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/183987; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 2106-04-9,Some common heterocyclic compound, 2106-04-9, name is 3-Chloro-2-fluoroaniline, molecular formula is C6H5ClFN, 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.

6-ACETOXY-4- (3-CHLORO-2-FLUOROANILINO)-7-METHOXYQUINAZOLINE HYDROCHLORIDE 6-ACETOXY-4-CHLORO-7-METHOXYQUINAZOLINE (prepared as described in Example 25-5 of in WO01/66099, 6.00 g, 23.8 mmol) and 3-chloro-2-fluoroaniline (3.46 g, 23.8 mmol) were suspended in iso-propanol (200 ML). The mixture was heated to 80C under reflux for 3 hours. The solvent was evaporated; the residue was crystallised from acetonitrile, giving the product hydrochloride as a pale pink crystalline solid (8.16 g, 92%); H NMR : 2.37 (s, 3H), 4.00 (s, 3H), 7.34 (ddd, 1H), 7.48 (s, 1H), 7.52 (ddd, 1H), 7.61 (ddd, 1H), 8.62 (s, 1H), 8.86 (s, 1H) ; Mass Spectrum : 362. 4,364. 4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloro-2-fluoroaniline, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/28469; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 2106-04-9, These common heterocyclic compound, 2106-04-9, name is 3-Chloro-2-fluoroaniline, 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.

Sodium nitrite (9.7 g, 0.14 mol) was dissolved in 25 mL of water and added to the solution cooled to -5 C.3-chloro-2-fluoroaniline (20.0 g, 0.14 mmol) in trifluoroacetic acid (100 mL),Sodium azide (9.1 g, 0.14 mol) dissolved in 5 mL of water was added dropwise to the reaction solution, and the mixture was dropped.The reaction mixture was stirred at 0 C for 2 hr then quThe organic phase is dried and filtered.After concentration, the title compound (18.7 g) was obtained.Used directly in the next step.

The synthetic route of 2106-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan Kelun Botai Bio-pharmaceutical Co., Ltd.; Wu Yongyong; Song Zhiquan; Cai Jiaqiang; Zhu Jiawang; Wang Lichun; Wang Jingyi; (71 pag.)CN109867660; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 2106-04-9, These common heterocyclic compound, 2106-04-9, name is 3-Chloro-2-fluoroaniline, 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.

Will 25g compound 214.5g of compound 3,400 mL of isopropanol was added to the reaction flask.Warming up to reflux for 3 h,After the TLC detection reaction is completed, the temperature is lowered to 0 to 40 C, and suction filtration is performed.Then drying at 40 to 50 C to obtain 35 g of compound 4;

The synthetic route of 2106-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tonghua Normal College; Geng Xiaoyu; Xue Mingxing; Zang Hao; Liu Xuekun; Sun Renshuang; Xue Changsong; Zhang Haifeng; (13 pag.)CN109438423; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 2106-04-9, 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. 2106-04-9 name is 3-Chloro-2-fluoroaniline, 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.

General procedure: To a solution of (E)-N-(2-cyano-4-nitrophenyl)-N,N-dimethylformimidamide 17 (6.0 g, 2.7 mmol) and acetic acid (45 mL) was added 3-fluoroaniline (18a, 3.3 g, 3.0 mmol) at room temperature. The reaction mixture was heated up to reflux temperature for 1 h. After completion of the reaction, the resulting mixture was cooled to room temperature. The solid separated was filtered and washed with ether to give 19a, 6.5 g (83%);

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-2-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Article; Marvania, Bhavin; Lee, Pei-Chih; Chaniyara, Ravi; Dong, Huajin; Suman, Sharda; Kakadiya, Rajesh; Chou, Ting-Chao; Lee, Te-Chang; Shah, Anamik; Su, Tsann-Long; Bioorganic and Medicinal Chemistry; vol. 19; 6; (2011); p. 1987 – 1998;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 2106-04-9,Some common heterocyclic compound, 2106-04-9, name is 3-Chloro-2-fluoroaniline, molecular formula is C6H5ClFN, 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: A round-bottomed flask was charged with 2-bromoaniline or 2-fluoro-aniline (>3 g, 1.0 equiv) and potassium O-ethyl carbonodithioate(1.5-1.7 equiv). The mixture was dissolved in DMF (10 volumes) andheated to 120-130 C until the aniline was fully consumed (3-14 h).The reaction mixture was cooled to r.t. and filtered. The filtrate wasdiluted with H 2 O (50 volumes) and the pH was adjusted to 1-2 usingaqueous 2 M HCl. The solid precipitate was collected, washed withH 2 O and dried to yield the pure product.

The synthetic route of 2106-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wimmer, Laurin; Parmentier, Michael; Riss, Bernard; Kapferer, Tobias; Ye, Chao; Li, Lei; Kim, Hongyong; Li, Jialiang; Synthesis; vol. 50; 10; (2018); p. 2027 – 2032;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 2106-04-9, A common heterocyclic compound, 2106-04-9, name is 3-Chloro-2-fluoroaniline, molecular formula is C6H5ClFN, 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.

To a suspension of Intermediate 5 (100 g, 0.396 mol) in acetonitrile (4 L) was added 2-fluoro-3-chloroaniline (60.5 g, 0.416 mol) and the reaction mixture was heated to 80 C. overnight. The precipitate was collected by filtration and dried in vacuo to afford Intermediate 6 (181 g, 80% purity) as white solid which was used for next step directly without purification. 1H NMR (DMSO-d6 400 MHz): delta 8.93 (s, 1H), 8.82 (s, 1H), 7.67-7.63 (m, 1H), 7.59 (s, 1H), 7.56-7.52 (m, 1H), 7.39-7.35 (m, 1H), 4.02 (s, 3H), 2.39 (s, 3H).

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; ASTRAZENECA AB; LI, David Yunzhi; WANG, Jiabing; YANG, Zhenfan; ZENG, Qingbei; ZHANG, Xiaolin; US2014/255428; (2014); 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. 2106-04-9, name is 3-Chloro-2-fluoroaniline, A new synthetic method of this compound is introduced below., Quality Control of 3-Chloro-2-fluoroaniline

3.25 ml phosphorus oxychloride are added dropwise to 6.50 g 6-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-7-methoxy-3H-quinazolin-4-one in 65 ml acetonitrile under an argon atmosphere. Then the reaction mixture is heated to 40 C., combined dropwise with 5.00 ml triethylamine and refluxed for 2 h. After cooling to ambient temperature 1.40 ml triethylamine and 2.60 ml 3-chloro-2-fluoro-aniline, dissolved in 5 ml acetonitrile, are added and the reaction mixture is stirred overnight at 40 C. Then a further 0.70 ml of 3-chloro-2-fluoro-aniline dissolved in 2 ml acetonitrile are added dropwise and the reaction mixture is stirred for a further 10 h. After cooling to ambient temperature the precipitate formed is suction filtered, taken up in 1 N hydrochloric acid, combined with 6 N isopropanolic hydrochloric acid and stirred at ambient temperature until the ketal cleaving is complete. The precipitate formed is suction filtered and combined with methylene chloride and 1 N sodium hydroxide solution. The aqueous phase is separated off and extracted with methylene chloride, the combined extracts are evaporated down and the flask residue is brought to crystallisation with diisopropylether.Yield: 5.90 g (73% of theory)Mass spectrum (ESI+): m/z=416, 418 [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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/46148; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2106-04-9, name is 3-Chloro-2-fluoroaniline, 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 2106-04-9, Product Details of 2106-04-9

To a stirred solution of A1C13 (10.0 g, 75.01 mmol) and BC13 (1Mm n-hexane, 74 mL,75.01 mmol) in CH2C12 (80 mL) was added 3-chloro-2-fluoroaniline 1 (9.0 g, 6.18 mmol) followed by a solution of chloroacetonitrile (11.6 g, 153.64 mmol) in CH2C12 (20 mL) at 0 C under inert atmosphere. The reaction mixture was allowed to stir at RT for 30 minutes and heated to reflux for additional 14 h. The reaction mixture was then cooled to 0 C, added aqueous 3 N HC1 (100 mL) and raised the temperature to reflux and stirred for 3 h. The mixture was cooled RT, diluted with water (50 mL) and extracted with CH2C12 (2 x 150 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to obtain the crude. The crude was purified by triturating with n-pentane to afford compound 2 (4.5 g, 33%) as an off-white solid. 1H NMR (500 MHz, DMSO-d6): (57.61 (d, J= 9.0 Hz, 1H), 7.35 (br s, 2H), 6.72 (d, J 9.0 Hz, 1H), 5.06 (s, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-2-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; PHARMAKEA, INC.; HUTCHINSON, John, Howard; LONERGAN, David; HUANG, Fei; ROWBOTTOM, Martin; CALDERON, Imelda; WO2015/48301; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics