Tag: M.W=100-200

Related Products of 115279-73-7, A common heterocyclic compound, 115279-73-7, name is 1-(4-Aminophenyl)cyclopentanecarbonitrile, molecular formula is C12H14N2, 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 500 ml four-necked flask equipped with a stirrer, a thermometer and a distillation system, 100 g of toluene and 11.2 g (0.06 mol) of 1-(4-aminophenyl)cyclopentylcarbonitrile (V) were added. 0.25 g of 4-dimethylaminopyridine, maintaining an internal temperature of 95-105 C. A solution of 12.9 g (0.05 mol) of ethyl 2-[(pyridin-4-ylmethyl)amino]-3-pyridinecarboxylate (IV2) prepared in Example 4 and 30 g of toluene was added dropwise, and the mixture was dropped over 2 hours. Thereafter, the reaction was stirred at 110-115 C for 5 hours, and the formed ethanol was distilled off. After the reaction was completed, the temperature was lowered to 20-25 C, filtered, and the filter cake was washed with 20 g of toluene, the filtrate was combined, and toluene was distilled off under reduced pressure. The tert-butyl ether was recrystallized, filtered and dried to give 18.1 g of a white solid powder of eptatinib (I), yield 91.2%, liquid phase purity 99.92%, melting point 158.5-160.0 C.

The synthetic route of 115279-73-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xin Fa Pharmaceutical Co., Ltd.; Cui Qingrong; Liu Yuesheng; Qu Hu; Lv Qiangsan; Ju Lizhu; (10 pag.)CN109020881; (2018); A;,
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Adding a certain compound to certain chemical reactions, such as: 41963-20-6, name is 4-Bromo-3-methylbenzonitrile, 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 41963-20-6, Recommanded Product: 4-Bromo-3-methylbenzonitrile

To a solution of 17 (10.0 g, 49.5 mmol) in carbon tetrachloride (200 mL) were added N-bromosuccinimide (8.81 g, 49.5 mmol) and 2,2′-azobis(isobutyronitrile) (414 mg, 5 mol %), and the mixture was refluxed for 3 h. Water was added, and the mixture was extracted with chloroform. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. To the residue were added dimethylformamide (150 mL) and sodium acetate (20.5 g, 250 mmol), and the mixture was stirred at 80 C. overnight. Water was added, and the mixture was extracted with ether. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. To the residue was added methanol (150 mL) and 1 mol/L sodium hydroxide (50 mL), and the mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated to about a third of volume under reduced pressure. Water and hydrochloric acid were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (3:1 hexane/ethyl acetate) followed by trituration with dichloromethane to give 2-bromo-5-cyanobenzyl alcohol (4.63 g, overall 44%): 1H NMR (300 MHz, DMSO-d6) delta (ppm) 4.51 (d, J=5.9 hz, 2H), 5.67 (t, J=5.6 Hz, 1H), 7.67 (dd, J=8.2, 2.0 Hz, 1H), 7.80 (s, J=8.2 Hz, 1H), 7.83 (d, J=2.0 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-3-methylbenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Anacor Pharmaceuticals; US2007/265226; (2007); A1;,
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Some common heterocyclic compound, 34662-30-1, name is 3-Chloro-5-nitrobenzonitrile, molecular formula is C7H3ClN2O2, 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-5-nitrobenzonitrile

3-Chloro-5-nitrobenzonitrile was reduced to 3-amino-5-chlorobenzonitrile by treating with 6 equivalents of SnCl2 dihydrate in DMF at RT overnight. The product was purified by chromatography over silica gel (40% yield). LCMS (Cond. A) RT 1.61 min., MH+ 153. 1H NMR (500 MHz, CDCl3) delta 6.97 (s, 1H), 6.84 (t, J=2.0 Hz, 1H), 6.77 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 34662-30-1, its application will become more common.

Reference:
Patent; Gerritz, Samuel; Shi, Shuhao; Zhu, Shirong; US2006/287287; (2006); A1;,
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Electric Literature of 1194-65-6, These common heterocyclic compound, 1194-65-6, name is 2,6-Dichlorobenzonitrile, 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.

A mixture of 2,6-dichlorobenzonitrile(100 g, 581mmol),triethylamine(64.5 g, 640mmol) and (NH4)2S (20% aqueous solution, 217 mL, 640mmol) in pyridine (500 mL) was stirred at 50 C for 4 h.The mixture was concentrated under reduced pressure.The residue was dissolved in water (400 mL) and extracted withEtOAc(3 x 300 mL).The combined organic extract was washed with brine (100 mL), dried over Na2SO4, and concentrated under reduced pressure.The residue was re-crystallized withEtOAc/petroleum ether to afford the desired intermediate as a pale yellow solid (105 g, 88% yield).LCMS (ESI) m/z: 206.0 [M+H+].

The synthetic route of 1194-65-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liang, Jun; Van Abbema, Anne; Balazs, Mercedesz; Barrett, Kathy; Berezhkovsky, Leo; Blair, Wade S.; Chang, Christine; Delarosa, Donnie; DeVoss, Jason; Driscoll, Jim; Eigenbrot, Charles; Goodacre, Simon; Ghilardi, Nico; MacLeod, Calum; Johnson, Adam; Bir Kohli, Pawan; Lai, Yingjie; Lin, Zhonghua; Mantik, Priscilla; Menghrajani, Kapil; Nguyen, Hieu; Peng, Ivan; Sambrone, Amy; Shia, Steven; Smith, Jan; Sohn, Sue; Tsui, Vickie; Ultsch, Mark; Williams, Karen; Wu, Lawren C.; Yang, Wenqian; Zhang, Birong; Magnuson, Steven; Bioorganic and Medicinal Chemistry Letters; vol. 27; 18; (2017); p. 4370 – 4376;,
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Application of 87376-25-8, These common heterocyclic compound, 87376-25-8, name is 2-Amino-4-nitrobenzonitrile, 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: In a typical procedure, 5-aryl-1H-tetrazoles (1-24) were synthesized by adding aryl nitriles (1 eq.), sodium azide (1.2 eq.), and ammonium chloride (1 eq.) in solvent, the mixture was refluxed for 24 h. Progress of the reaction was monitored by thin layer chromatography. After completion of the reaction, 2.5 mL of 2M NaOH was added and the solution was stirred for half an hour. The reaction mixture was concentrated on reduced pressure, and dissolved in water. 3M HCl was added to the reaction mixture until precipitates formed. The precipitates were filtered and washed with distilled water. The yields of title compounds were found to be moderate to high.

Statistics shows that 2-Amino-4-nitrobenzonitrile is playing an increasingly important role. we look forward to future research findings about 87376-25-8.

Reference:
Article; Fatima, Itrat; Zafar, Humaira; Khan, Khalid Mohammed; Saad, Syed Muhammad; Javaid, Sumaira; Perveen, Shahnaz; Choudhary, M. Iqbal; Bioorganic Chemistry; vol. 79; (2018); p. 201 – 211;,
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50846-36-1, name is 2-Amino-2-methylpropanenitrile hydrochloride, 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. COA of Formula: C4H9ClN2

To a solution of Compound 20 (20 mg), 2-amino-2-methylpropanenitrile hydrochloride (9.32 mg, 0.077 mmol) and HATU (22.05 mg) in DMF (2 mL) was added iPr2NEt (0.027 mL). The mixture was stirred at room temperature for 4 hours. The product was isolated by preparative HPLC system

The synthetic route of 50846-36-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Wang, Tao; Eastman, Kyle J.; Zhang, Zhongxing; Parcella, Kyle E.; Yin, Zhiwei; Kadow, John F.; US2015/266886; (2015); A1;,
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Application of 194853-86-6, These common heterocyclic compound, 194853-86-6, name is 4-Fluoro-2-(trifluoromethyl)benzonitrile, 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.

Weigh 508mg of 5,5-dimethylhein into eggplant-shaped bottles, add 5mL of DMF with stirring to completely dissolve it, then add 220mg of K2CO3 (1eq), stir at 45 C for half an hour to make them mix well. Finally, the DMF solution of 4-fluoro-2-trifluoromethylbenzonitrile (300 mg) was slowly added, and stirred under heating for 5 hours. After the reaction was fully completed, it was cooled to room temperature and diluted with 30 mL of ethyl acetate. It was extracted 3 times with 20 mL of saturated ammonium chloride aqueous solution and once with saturated brine. The organic layer was dried over anhydrous magnesium sulfate for 6 h, filtered with suction, and concentrated. Finally, 200-300 mesh column chromatography was performed to obtain 330 mg of a white solid. Yield 79%.

The synthetic route of 194853-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhengzhou University; Ke Yu; Xie Hang; Liu Hongmin; Xu Xia; Liang Jianjia; (25 pag.)CN110759897; (2020); A;,
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Related Products of 10406-25-4, 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. 10406-25-4, name is 4-(Aminomethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: CDI (112 mg, 0.69 mmol) was added under nitrogen to a solution of 6 (200 mg, 0.62 mmol) in dry methylene chloride (15 mL). The solution was stirred at room temperature for 1 h, then (4-fluorophenyl)methanamine (116 mg, 0.93 mmol) was added, and stirred at room temperature under nitrogen or 24 h. After the complete conversion of the starting material, the reaction was quenched with 1 M HCl. The aqueous phase was extracted with methylene chloride (3 * 50 mL). The combined organic phases were washed with brine until neutral pH, dried on Na2SO4, filtered, and the solvent was eliminated under reduced pressure to give 7a (240 mg, 90%).

The synthetic route of 4-(Aminomethyl)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tian, Yuanxin; Zhang, Tingting; Long, Lifan; Li, Zhonghuang; Wan, Shanhe; Wang, Guangfa; Yu, Yonghuan; Hou, Ju; Wu, Xiaoyun; Zhang, Jiajie; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 182 – 199;,
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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. 38469-83-9, name is 4-Methoxy-2-nitrobenzonitrile, A new synthetic method of this compound is introduced below., category: nitriles-buliding-blocks

EXAMPLE 50 2′-Carbamoyl-5′-methoxyoxanilic acid ethyl ester. 91 2-Nitro-4-methoxybenzonitrile (12.8 g) is reduced in a manner similar to example 40, giving 9.0 g of 2-amino-p-anisamide, m.p. 152-156C., after crystallization from water. Elemental Analysis for C8 H10 N2 O2: Calc’d: C, 57.82; H, 6.07; N, 16.86. Found: C, 58.60; H, 5.76; N, 16.65.

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; American Home Products Corporation; US3966965; (1976); A;,
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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. 5922-60-1, name is 2-Amino-5-chlorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H5ClN2

2-amino-5-chlorobenzonitrile (152.6 mg, 1.0 mmol) was sequentially added to a 100 mL high pressure sealed tube, benzyl alcohol(129.6 mg, 1.2 mmol, 1.2 equiv.), cesium hydroxide monohydrate (167.9 mg, 1.0 mmol), an air ball was added to the closed tube.Stir at 120 C for 36 h, after monitoring the reaction by TLC or GC-MS,The product was purified by column chromatography. The isolated yield was 65%.

According to the analysis of related databases, 5922-60-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Yangzhou University; Xu Qing; Wang Qi; Lv Miao; Li Yang; Cao Hongen; (16 pag.)CN109879820; (2019); A;,
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