Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 6393-40-4, name is 4-Amino-3-nitrobenzonitrile, belongs to nitriles-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 6393-40-4, Recommanded Product: 6393-40-4

General procedure: 4.2. General procedure for the indium-mediated reductivecyclization of 2-nitroanilines to prepare quinoxalines A mixture of the 2-nitroaniline derivative (1.0 mmol), dione (1.0or 2.0 mmol), indium (0.574 g, 5.0 mmol), and acetic acid (0.300 g,5 mmol or 0.600 g,10 mmol) or indium chloride (0.221 g,1 mmol or0.265 g,1.2 mmol) in methanol (5 mL) or toluene (5 mL) was stirredat 50 C, 80 C, or reux under a nitrogen atmosphere. After com-pletion of the reaction, the reaction mixture was diluted with ethylacetate (30 mL), ltered through Celite, and the ltrate was pouredinto 10% NaHCO3 (30 mL) and extracted with ethyl acetate(30 mL3). The combined organic extracts were dried over MgSO4,ltered, and concentrated. The residue was eluted with ethyl ace-tate/hexane (v/v10/90) through a silica gel column to give thecorresponding pure quinoxaline. Quinoxaline structures werecharacterized by 1H NMR, 13C NMR, FTIR, and GCeMS, and weremostly known compounds. For unknown compounds, elementalanalysis data were additionally obtained. 4.2.1. 2,3-Dimethylquinoxaline (5).19,31aef Yield 87%. Yellow solid,mp 109e110 C (lit.31f mp 105 C). TLC (10% ethyl acetate/hexane) Rf0.30; 1H NMR (400 MHz, CDCl3) d 7.91 (dd, 2H, J6.3, 3.5 Hz), 7.59(dd, 1H, J6.3, 3.5 Hz), 2.66 (s, 6H); 13C NMR (100 MHz, CDCl3)d 153.4, 141.0, 128.7, 128.2, 23.1; IR (KBr) 3109, 3078, 3030, 2995,2953, 2914, 1490, 1398, 1164 cm1;GCeMS m/z (rel intensity) 158(M, 99), 117 (100), 76 (28), 50 (12).

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; Go, Ahra; Lee, Geunsoo; Kim, Jaeho; Bae, Seolhee; Lee, Byung Min; Kim, Byeong Hyo; Tetrahedron; vol. 71; 8; (2015); p. 1215 – 1226;,
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Application of 1885-38-7, 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. 1885-38-7 name is (E)-Cinnamonitrile, 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: In a Schlenck flask filled with gaseous carbon dioxide, to a stirred THF (1.5 mL) solution of the alpha,beta-unsaturated compound 1 (0.25 mmol) and bis(acetylacetonato)cobalt(II) (conditions A: 3.2 mg, 5 mol %; conditions B: 6.4 mg, 10 mol %) was added a 1.0 M n-hexane solution of diethylzinc (conditions A: 0.5 mL, 2 equiv; conditions B: 1.0 mL, 4 equiv) at 0 C, then the reaction mixture was stirred at 20 C for 1-48 h. After checking the completed reaction by TLC analysis, the reaction mixture was quenched with a 1.0M hydrochloric acid diethyl ether solution (conditions A: 1.5 mL, 6 equiv; conditions B: 3.0 mL, 12 equiv) at 0 C. The organic layer was extracted with diethyl ether, washed with brine, dried over sodium sulfate and concentrated in vacuum. The residue was purified by silica gel column chromatography (Hexanes:AcOEt:HCOOH = 1:1:0.003) to afford the desired carboxylic acid 2. The resulting compound was diluted with a mixed solution (6.25 mL, diethyl ether:MeOH = 5:1) and methylated with trimethylsilyldiazomethane in n-hexane (ca. 0.6M solution, (1.04 mL, 2.5 equiv)). After purification by chromatography on silica gel, the corresponding methyl carboxylate was isolated.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (E)-Cinnamonitrile, and friends who are interested can also refer to it.

Reference:
Article; Hayashi, Chika; Hayashi, Takuo; Yamada, Tohru; Bulletin of the Chemical Society of Japan; vol. 88; 6; (2015); p. 862 – 870;,
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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. 935-02-4, name is 3-Phenylpropiolonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Phenylpropiolonitrile

General procedure: To a solution of cyanoacetylenes (0.4mmol) with N-tosylimines (0.2 mmol) in toluene (2 mL) was added Ph3P (0.2mmol). The mixture was then stirred at 110 C for 36 h in a reaction flask. Thenthe solvent was removed in vacuo and residue was purified by columnchromatography on silica gel to give the desired annulation product.

The synthetic route of 935-02-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Jinfeng; Zhang, Qi; Ji, Xin; Meng, Ling-Guo; Synlett; vol. 30; 9; (2019); p. 1095 – 1099;,
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Reference of 873-32-5,Some common heterocyclic compound, 873-32-5, name is 2-Chlorobenzonitrile, molecular formula is C7H4ClN, 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: Typically, an aryl chloride (2.0 mmol), phenylboronic acid (3.0 mmol), Pd(at)NPad2-1.0 catalyst (5.4 mg, 0.02 mol% Pd), K2CO3 (552.8 mg, 4.0 mmol) and 4.0 mL of i-PrOH/water (1:1) were added into a 25 mL pressure tube under Ar. The reaction mixture was stirred at 100 C for 18 h in an oil bath. After the reaction mixture cooled down to room temperature, the product was isolated by column with silica gel and analyzed by 1H NMR.

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

Reference:
Nitrile – Wikipedia,
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Electric Literature of 1897-52-5, A common heterocyclic compound, 1897-52-5, name is 2,6-Difluorobenzonitrile, molecular formula is C7H3F2N, 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.

Example 156A 2-Fluoro-6-(1H-1,2,4-triazol-1-yl)benzonitrile Under argon, 2,6-difluorobenzonitrile (1.00 g, 7.19 mmol) was dissolved in dimethylsulfoxide (4 mL), and 1,2,4-triazole (0.52 g, 7.48 mmol) and cesium carbonate (2.44 g, 7.48 mmol) were added. The mixture was stirred at 50 C. for 5 h. After cooling to RT, water (20 mL) was added and stirring was continued for 15 min. The precipitate was filtered and washed with water (10 mL). The solid was taken up in dichloromethane/water and extracted with dichloromethane. The combined organic phases were washed with brine, and concentrated in vacuo. Purification via column chromatography (silica gel, cyclohexane/ethyl acetate, Gradient) afforded the title compound (0.25 g, 18% of theory). LC-MS (Method 1B): Rt=0.62 min, MS (ESIPos): m/z=189 [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; BAYER PHARMA AKTIENGESELLSCHAFT; Hassfeld, Jorma; KINZEL, Tom; Koebberling, Johannes; CANCHO GRANDE, Yolanda; BEYER, Kristin; Roehrig, Susanne; Koellnberger, Maria; SPERZEL, Michael; BURKHARDT, Nils; SCHLEMMER, Karl-Heinz; STEGMANN, Christian; SCHUHMACHER, Joachim; WERNER, Matthias; ELLERMANN, Manuel; US2015/126449; (2015); A1;,
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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. 326-62-5, name is 2-(2-Fluorophenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H6FN

Example 1a Preparation of 2-(2-fluorophenyl)-2-methylpropanenitrile To a 500 mL 3-neck round bottom flask with an attached addition funnel that has been purged with dry N2, was added 2-fluorophenylacetonitrile (11.0 g, 81.4 mmol) and anhydrous THF (70 mL). The reaction solution was cooled to -10 C. prior to dropwise addition of a 1.0 M potassium tert-butoxide solution (195 mL, 2.4 molar equiv) in THF. The reaction solution was stirred at -10 C. for 20 min prior to addition of iodomethane (15.2 mL, 244 mmol). The reaction solution was allowed to stir warming to room temperature for 4 hr. The reaction solution was quenched by addition of aq NH4Cl and diluted with EtOAc (200 mL). The organic phase was partitioned, washed with aq NH4Cl, dried over Na2SO4, filtered, concentrated in vacuo and chromatographed through a 240 g SiO2 column on the Biotage SP-1 using a solvent gradient of 100% Hx to 50% EtOAc to afford 10.1 g (76% yield) of title product. GCMS m/z=163 [M]+.

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 326-62-5.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; EXELIXIS PATENT COMPANY LLC; Busch, Brett B.; Stevens, JR., William C.; Kick, Ellen K.; Zhang, Haiying; Bollu, Venkataiah; Martin, Richard; Mohan, Raju; US2015/299136; (2015); A1;,
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42872-74-2, name is 3-Bromo-4-methylbenzonitrile, belongs to nitriles-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. name: 3-Bromo-4-methylbenzonitrile

[0097] The solution of 3-bromo-4-methylbenzonitrile (3) (2.0 g, 10 mmol), in DMF (12 mL) with Bis(pinacolato)diboron (3.4 g, 13 mmol), and Pd(OAc)2 (0.5 g, 2 mmol), and KOAc (3 g, 30 mmol) was microwaved for 3 h at 80C. The mixture was then diluted with H2O (25 mL) and extracted with EtOAc (2 x 30 mL). [0098] The organic phase was collected and dried over Na2SO4 Column chromatography (in Hexane/Ethyl acetate 9:1) afforded 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (B) as an oil, which solidified during the drying in vacuo (yield: 96%)

The synthetic route of 42872-74-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; CHEN, Shoujun; ZHANG, Junyi; JIANG, Jun; KOWALCZYK-PRZEWLOKA, Teresa; XIA, Zhiqiang; ZHANG, Shijie; WO2013/63385; (2013); A1;,
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Synthetic Route of 38487-86-4,Some common heterocyclic compound, 38487-86-4, name is 2-Amino-4-chlorobenzonitrile, molecular formula is C7H5ClN2, 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.

2-Amino-4-chlorobenzonitrile(153 mg, 1 mmol), [Cp * IrCl2] 2 (8 mg, 0.01 mmol, 1 mol%),Butyraldehyde oxime (96 mg, 1.1 mmol), p-xylene (2.0 mL) were sequentially added to a 25 mL Schlenk reaction flask.After the mixture was reacted at 70 C for 12 hours, cooled to room temperature, and then added to a 25 mL Schlenk flaskBenzaldehyde (117 mg, 1.1 mmol) was added. The mixture was further reacted at 110 C for 4 hours and then cooled toThe solvent was removed under vacuum at room temperature. Then through several petroleum ether washing, filtration, drying to be pure goalCompound, yield: 91%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-4-chlorobenzonitrile, its application will become more common.

Reference:
Patent; Nanjing University of Science and Technology; Zhao Wei; Wang Rongzhou; Li Feng; (17 pag.)CN106478525; (2017); A;,
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Synthetic Route of 50397-74-5, The chemical industry reduces the impact on the environment during synthesis 50397-74-5, name is 4-Amino-3-bromobenzonitrile, I believe this compound will play a more active role in future production and life.

Diethyl ethoxymethylenemalonate (8.23 g, 38.1 mmol) was added to a solution of 1 (5.00 g, 25.4 mmol) in 30 mL of toluene. The mixture was then heated to reflux overnight with the condenser open to the air. The resulting solution was cooled down to room temperature and poured into 100 mL of hexanes. The white precipitate was collected and washed with hexanes (3 * 30 mL) to yield 11.9 g of an off-white solid as the desired product. MS ESI (m/z) 367 (M + 1)+; 1H NMR (CDCl3, 300 MHz): delta 11.44 (d, 1H, J = 12.6 Hz), 8.44 (d, 1H, J = 12.9 Hz), 7.86 (d, 1H, J = 1.8 Hz), 7.63 (dd, 1H, J1 = 1.8 Hz, J2 = 8.7 Hz), 7.33 (d, 1H, J = 8.4 Hz), 4.35 (q, 2H, J = 6.9 Hz), 4.27 (q, 2H, J = 6.9 Hz), 1.38 (t, 3H, J = 6.9 Hz), 1.33 (t, 3H, J = 6.9 Hz).

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-Amino-3-bromobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fiorito, Jole; Saeed, Faisal; Zhang, Hong; Staniszewski, Agnieszka; Feng, Yan; Francis, Yitshak I.; Rao, Sudha; Thakkar, Devarshi M.; Deng, Shi-Xian; Landry, Donald W.; Arancio, Ottavio; European Journal of Medicinal Chemistry; vol. 60; (2013); p. 285 – 294;,
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Electric Literature of 115661-37-5, A common heterocyclic compound, 115661-37-5, name is 2-Amino-3-fluorobenzonitrile, molecular formula is C7H5FN2, 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 100 mL of the round bottom flask was added 1 g (about 7.35 mmol) of 2-amino-3-fluorobenzonitrile, 4.88 mL (about 36.73 mmol) of N,N-dimethylformamide dimethyl acetal and 15 mL of solvent methanol. The reaction in the round bottom flask was then stirred under reflux for 6 hours. The solvent and excess reactants are removed by distillation under reduced pressure. Intermediate (E)-N’-(2-cyano-6-fluorophenyl)-N,N-dimethylformamidine 1.4 g is obtained. The yield is 99%,

The synthetic route of 115661-37-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhengzhou University; Liu Hongmin; Yu Bin; Yuan Shuo; Zhang Danqing; (31 pag.)CN110078675; (2019); A;,
Nitrile – Wikipedia,
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