Category: 202197-26-0

Reference of 202197-26-0, A common heterocyclic compound, 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, molecular formula is C13H11ClFNO, 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 round bottle, isopropanol (20 mL), 3-bromoaniline (0.62 g, 3.6 mmol), 4-cholo-6-iodo-quinazoline 15 (0.87 g, 3 mmol) andtriethylamine (0.36 g, 3.6 mmol) was added. The resulting reactionmixture was stirred at room temperature for 6 h and then at refluxfor another 3 h. After cooling to room temperature, the yellow solidwas collected by suck filtration, wash with isopropanol, water andether sequentially, and dried at 50 C to afford compound 12a as ayellow solid (0.74 g, 69% yield)

The synthetic route of 202197-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lin, Songwen; Li, Yingbo; Zheng, Yufen; Luo, Laichun; Sun, Qi; Ge, Zemei; Cheng, Tieming; Li, Runtao; European Journal of Medicinal Chemistry; vol. 127; (2017); p. 442 – 458;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 202197-26-0, 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. 202197-26-0 name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, 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.

Roschangar et al. ,Use of lithium N,O-dimethylhydroxylamide as an efficient in situ protecting agent for aromatic aldehydes. Tertrahedron 2002, 58, 1657-1666). Preparation analogous (Nishino et al.; Process for producing 4-aminoquinazoline compound by chlorination of quinazolin-4-one or its derivative and animation. 2003) as follows: To a mixture of 6-iodo-lH-quinazolin-4-one (10) (6.8Og; 25.0 mmol), toluene (5.0 mL) and POCl3 (27.5 mmol; 2.60 mL) carefully triethylamine (27.5 mmol; 3.81 mL) was added. The mixture was heated to 80 0C for 2 h, cooled to room temperature, a solution of 3-chloro~4-(3- fluorobenzyloxy)phenylamine (15) (27.50 mmol; 6.92 g) in 2~butanone (20.0 mL) added and the mixture stirred at 80 0C for another hour. The mixture was cooled to 00C, the yellow precipitate was filtered off and added to a NaOH solution (IN; 150 mL) by stirring. After 30 min the yellow solid was filtered off, washed with water and a small amount of acetone and dried in vacuo. Yield (8.38 g; 66%) analytical pure sample. 1H-NMR (DMSO-[D6]): delta (ppm) = 5.26 (s, 2H), 7.15-7.22 (m, IH), 7.27 (d, IH, J = 9.1 Hz), 7.29-7.35 (m, 2H), 7.43-7.51 (m, IH), 7.56 (d, IH, J = 8.8 Hz), 7.74 (dd, IH, J = 9.1 Hz, 4J = 2.5 Hz), 8.02 (d, IH5 4J = 2.5 Hz), 8.12 (dd; IH, J = 8.8 Hz, 4J = 1.7 Hz)5 8.62 (s, IH), 8.96 (d, 4J = 1.7 Hz), 9.90 (s, IH, exchangeable).

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

Reference:
Patent; 4SC AG; WO2009/63054; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 202197-26-0, 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. 202197-26-0 name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, 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: Followed we described previously, substituted aniline (3.3 mol). The reaction mixture was heated to 130 and stirred for 15 min. The reaction mixture was then cooled to 25 . The acetic acid was evaporated. The reaction mixture was quenched in ice-water (25.0 mL), and adjusted pH~9 with ammonia solution. The mixture was stirred for 0.5 h. The precipitated product was filtered, and the filter cake was washed with water (3 × 10 mL) to afford crude product. The crude product was chromatographed by silica gel, eluting with EtOAc/PE (1:4) to afford residue 13a-13c as white solid (yield 84.3% ~ 92.5%). 1.2.1.1 4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-6-iodoquinazoline (13a) White power, yield: 92.5%.

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

Reference:
Article; Zhang, Yaling; Gao, Hongliang; Liu, Renjie; Liu, Juan; Chen, Li; Li, Xiabing; Zhao, Lijun; Wang, Wei; Li, Baolin; Bioorganic and Medicinal Chemistry Letters; vol. 27; 18; (2017); p. 4309 – 4313;,
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. 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, A new synthetic method of this compound is introduced below., COA of Formula: C13H11ClFNO

General procedure: Acetic acid (2.0 mL) and aniline derivatives (1.10mmol) was added to 6 (1.00 mmol). The mixturewas heated to 125-130 C andstirred for 15 min. The reaction mixture was then cooled to 25 C.The acetic acid was evaporated. To the reaction mixture, ice-water(10 mL) was added and adjusted pH to 9 with ammonium hydroxide.The mixture was stirred for 0.5 h. The precipitated productwas filtered, and the filtered cake was washed with water(3 x 10 mL) to afford crude product. The crude product was chromatographedby silica gel, eluting with EtOAc/petroleum ether(1:4) to afford 7a-7f (yield 82-94%) as white solid. 4.1.7.1 4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-6,7-bis(2-chloroethoxy)quinazoline (7a) Yield: 86%. 1H NMR (600?MHz, DMSO-d6) delta(ppm): 9.47 (s, 1H), 8.48 (s, 1H), 7.97 (d, J?=?2.6?Hz, 1H), 7.91 (s, 1H), 7.71 (dd, J?=?8.9, 2.6?Hz, 1H), 7.50-7.46 (m, 1H), 7.35-7.31 (m, 2H), 7.28 (s, 1H), 7.26 (s, 1H), 7.20-7.16 (m, 1H), 5.25 (s, 2H), 4.48-4.45 (m, 4H), 4.08 (t, J?=?5.5?Hz, 2H), 4.04 (t, J?=?5.0?Hz, 2H). 13C NMR (151?MHz, DMSO-d6) delta(ppm): 162.2 (d, 1JC-F?=?243.7?Hz), 156.3, 153.2, 153.1, 149.5, 147.5, 147.0, 139.7, 139.6, 133.4, 130.5 (d, 3JC-F?=?8.3?Hz), 124.0, 123.3 (d, 4JC-F?=?2.6?Hz), 122.1, 121.1, 114.6 (d, 2JC-F?=?20.9?Hz), 114.3, 114.0 (d, 2JC-F?=?21.9?Hz), 109.0 (d, 3JC-F?=?8.6?Hz), 104.7, 69.5, 69.4, 68.9, 42.7, 42.6.

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:
Article; Zhang, Yaling; Chen, Li; Xu, Hongjiang; Li, Xiabing; Zhao, Lijun; Wang, Wei; Li, Baolin; Zhang, Xiquan; European Journal of Medicinal Chemistry; vol. 147; (2018); p. 77 – 89;,
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. 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., name: 3-Chloro-4-((3-fluorobenzyl)oxy)aniline

1.20 g (5.7 mmol) of 4-chloro-6-nitro-quinazoline (prepared by referring to WO 2007/082434) and 1.37 g (5.6 mmol) of 4-(3-fluoro-benzyloxy)-3-chloro-aniline (prepared by referring to WO 2007/082434) were dissolved in 80 mL of isopropanol and refluxed for 3 hours. A large amount of yellow solid was precipitated from the system, and was filtered. The filter cake was washed with a saturated sodium bicarbonate solution till pH=8 and dried under vacuum to obtain 1.62 g (3.75 mmol) of yellow solid, which was identified as the compound 4-[3-chloro-4-(3-fluoro-benzyloxy)phenylamino]-6-nitro-quinazoline with a yield of 67%.1H-NMR (400 MHz, CDCl3): delta11.30 (1H, br), 9.54-9.48 (1H, m), 8.45-8.41 (1H, m), 8.31-8.25 (1H, m), 7.98-7.89 (1H, m), 7.50-7.47 (1H, m), 7.35-7.26 (1H, m), 7.05-6.96 (1H, m), 6.90-6.80 (2H, m), 7.74-7.60 (2H, m), 4.84 (2H, s).

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 202197-26-0.

Reference:
Patent; Guo, Jianhui; Jiang, Yong; US2012/4249; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 202197-26-0, 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. 202197-26-0 name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, 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.

3-Chloro-4-((3-fluorobenzyl)oxy)aniline (12.58 g, 50 mmol) was added to 100 ml of toluene and stirred well.Thereafter, 0.4 g of acetic acid (as a catalyst) was added, followed by dropwise addition of triethyl orthoformate (3.8 g, at room temperature using an addition funnel.25 mmol), after the addition of the Dean-Stark apparatus, the reaction mixture was placed in an oil bath and heated to 80 C for 1 h.The ethanol was collected by a Dean-Stark apparatus; then the temperature was raised to 110 C for 2 h, and after the reaction was completed, it was cooled to room temperature and placed in an ice bath.The solid was precipitated, filtered, and the filter cake was washed with a little toluene to give (E)-N’-(3-chloro-4-((3-chlorobenzyl)oxy)phenyl)-N-(3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)carboxamidine 12.4 g, yield 93.7%. The HPLC purity was 99.14%.

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

Reference:
Patent; Yancheng Normal College; Nanjing University Of Technology Dafeng Ocean Industrial Institute; Sun Yaquan; Zong Chaoyang; Gu Huiwen; (10 pag.)CN108440420; (2018); A;,
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. 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, A new synthetic method of this compound is introduced below., COA of Formula: C13H11ClFNO

A stirred suspension of 3H-6-iodoquinazolin-4-one (compound A) in toluene (5 vols) was treated with tri-n-butylamine (1.2 eq.) at 20 to 250C, then heated to 900C. Phosphorous oxychloride (1.1eq) was added, the reaction mixture was then heated to reflux. The reaction mixture was cooled to 500C and toluene (5vols) added. Compound C (1.03 eq.) was added as a solid, the slurry was warmed back to 900C and stirred for 1 hour. The slurry was transferred to a second vessel; the first vessel was rinsed with toluene (2vol) and combined with the reaction mixture. The reaction mixture was cooled to 700C and 1.0 M aqueous sodium hydroxide solution (16 vols) added dropwise over 1 hour to the stirred slurry maintaining the contents temperature between 68-72C. The mixture was stirred at 65-700C for 1 hour and then cooled to 200C over 1 hour. The suspension was stirred at 200C for 2 hours, the product collected by filtration, and washed successively with water (3 x 5 vols) and ethanol (IMS, 2 x 5 vols), then dried in vacuo at 50-600C. Volumes are quoted with respect of the quantity of Compound A used. Percent yield range observed: 90 to 95% as white or yellow crystals.

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; SMITHKLINE BEECHAM (CORK) LIMITED; WO2006/66267; (2006); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C13H11ClFNO

(I) Preparation of the compounds Example 1: Preparation of N-{4-[3-chloro-4-(3-fluoro-benzyloxy)phenylamino] quinazolin-6-yl}-acrylamide 3tep A: preparation of 4-[3-chloro-4-(3-fluoro-benzyloxy)phenylamino]-6-nitro-quinazoline 1.20 g (5.7 mmol) of 4-chloro-6-nitro-quinazoline (prepared by referring to WO 2007/082434) and 1.37 g (5.6 mmol) of 4-(3-fluoro-benzyloxy)-3-chloro-aniline (prepared by referring to WO 2007/082434) were dissolved in 80mL of isopropanol and refluxed for 3 hours. A large amount of yellow solid was precipitated from the system, and was filtered. The filter cake was washed with a saturated sodium bicarbonate aqueous solution till pH=8 and dried under vacuum to give 1.62g ( 3.75 mmol ) of yellow solid, which was identified as 4-[3-chloro-4-(3-fluoro-benzyloxy) phenylamino]-6-nitro-quinazoline with a yield of 67%. 1H-NMR (400MHz, CDCl3): delta 11.30(1H, br), 9.54-9.48(1H, m), 8.45-8.41(1H, m), 8.31-8.25(1H, m), 7.98-7.89(1H, m), 7.50-7.47(1H, m), 7.35-7.26 (1H, m), 7.05-6.96(1H, m), 6.90-6.80(2H, m), 7.74-7.60(2H, m), 4.84(2H, s).

The synthetic route of 202197-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Allist Pharmaceuticals, Inc.; EP2292234; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 202197-26-0, 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. 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of 14 (1.03 g, 5 mmol), 10 mL SOCl2 and five drops of DMF was stirred and refluxed for 6 h. Excess SOCl2 was removed under reduced pressure, gave the intermediate 15 without further purification. A mixture of intermediate 15 and aniline (5 mmol) dissolved in 15 mL isopropanol, 1 mL Et3N was added, the mixture was stirred at reflux for 4 h. the reaction mixture was allowed to cool to room temperature. The precipitate was collected and washed with isopropanol, water and ether in order, dried to provide the products 16a-c.

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, 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Li, Ri-Dong; Zhang, Xin; Li, Qiao-Yan; Ge, Ze-Mei; Li, Run-Tao; Bioorganic and Medicinal Chemistry Letters; vol. 21; 12; (2011); p. 3637 – 3640;,
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. 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., name: 3-Chloro-4-((3-fluorobenzyl)oxy)aniline

Step 2) N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-nitroquinazolin-4-amine A mixture of 4-chloro-6-nitroquinazoline (7.50 g, 35.8 mmol) and 3-chloro-4-((3-fluorobenzyl)oxy)aniline (9.00 g, 35.8 mmol) in isopropanol (150 mL) was heated to 80 C and stirred for 3.0 hours. The resulting mixture was then cooled to 20 C, and a yellow solid precipitated out. The mixture was filtered. The filter cake was washed with isopropanol (20 mL) and dried under vacuum to give the title compound as a yellow solid (8.50 g, 59.8%). The compound was characterized by the following spectroscopic data: MS (ESI, pos.ion) m/z : 425.8 [M+l]+; and NMR (400 MHz, CDC13) delta: 11.30 (brs, 1H), 9.54-9.48 (m, 1H), 8.45-8.41 (m, 1H), 8.31-8.25 (m, 1H), 7.98-7.89 (m, 1H), 7.50-7.47 (m, 1H), 7.35-7.26 (m, 1H), 7.05-6.96 (m, 1H), 6.90-6.80 (m, 2H), 7.74-7.60 (m, 2H), 4.84 (s, 2H).

According to the analysis of related databases, 202197-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; LIU, Bing; LIU, Jinlei; ZHANG, Jiancun; ZHENG, Changchun; WO2014/177038; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics