Author: Jessica.F

Reference of 115279-57-7, The chemical industry reduces the impact on the environment during synthesis 115279-57-7, name is 2-(4-Aminophenyl)-2-methylpropanenitrile, I believe this compound will play a more active role in future production and life.

18 g (62.6 mmol) of 6-bromo-4-chloro-3-nitro-quinoline (Example lc) and 11 g(68.9 mmol) of (2-(4-amino-phenyl)-2-methyl-propionitrile (Example le) are dissolved in 350 ml of acetic acid and stirred for 2 h. After this time, water is added and the yellow precipitate is filtered off and washed with H2O. The solid is dissolved in EtOAc-THF (1 : 1), washed with sat. aqueous NaHC03and dried over MgS04. The organic phase is evaporated to dryness to give the title compound as a yellow solid. ES-MS: 411, 413 (M + H)+, Br pattern; analytical HPLC: tret= 3.69 min (Grad 1).

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, 2-(4-Aminophenyl)-2-methylpropanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS PHARMA AG; INCYTE CORPORATION; VANNUCCHI, Alessandro M.; BOGANI, Costanza; BARTALUCCI, Niccolo; WO2013/23119; (2013); A1;,
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Synthetic Route of 6393-40-4, 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. 6393-40-4 name is 4-Amino-3-nitrobenzonitrile, 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: A 100-mL round-bottomed single-neck flask equipped with a condenser and a magnetic stir bar was charged with appropriated 4-substituted-2-nitroaniline (25.0mmol), 2,5-dimethoxytetrahydofurane (25.0mmol) and 40mL of glacial acetic acid. The flask was refluxed until disappearance of starting material (ca. 2 h). After the reaction mixture was cooled to rt, removal of the volatiles under reduced pressure gave the crude product which was purified by column-chromatography (Petroleum Ether/EtOAc=9:1 then 7:3) to give the desired 1-(4-substituted-2-nitrophenyl)-1H-pyrrole.

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

Reference:
Article; Primas, Nicolas; Suzanne, Peggy; Verhaeghe, Pierre; Hutter, Sebastien; Kieffer, Charline; Laget, Michele; Cohen, Anita; Broggi, Julie; Lancelot, Jean-Charles; Lesnard, Aurelien; Dallemagne, Patrick; Rathelot, Pascal; Rault, Sylvain; Vanelle, Patrice; Azas, Nadine; European Journal of Medicinal Chemistry; vol. 83; (2014); p. 26 – 35;,
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Related Products of 151-18-8, 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. 151-18-8 name is 3-Aminopropanenitrile, 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.

Example 2 N-(2-cyanoethyl)-3-[1-(2,4-dichlorophenyl)-2,3-dihydro-1H-indol-6-yl]benzamide To a solution of 3-[1-(2,4-dichlorophenyl)-2,3-dihydro-1H-indol-6-yl]benzoic acid (105 mg, 0.27 mmol) obtained in Reference Example 4 and DMTMM (94.3 mg, 0.32 mmol) in DMF (1.5 ml) was added 3-aminopropanenitrile (23.6 muL, 0.32 mmol), and the mixture was stirred at room temperature for 4 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the title compound (100 mg , yield 85%) as crystals. Melting point 148 – 154C. 1H-NMR (CDCl3) delta : 2.76 (2H, t, J = 6.3 Hz), 3.22 (2H, t, J = 8.3 Hz), 3.73 (2H, q, J = 6.2 Hz), 3.94 (2H, brs), 6.60 (2H, d, J = 1.5 Hz), 6.99 (1H, dd, J = 7.6, 1.6 Hz), 7.21 – 7.29 (2H, m), 7.39 (1H, d, J = 8.5 Hz), 7.45 (1H, t, J = 7.7 Hz), 7.51 (1H, d, J = 2.3 Hz), 7.62 – 7.69 (2H, m), 7.89 (1H, t, J = 1.7 Hz).

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2298731; (2011); A1;,
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Application of 875664-25-8, 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 875664-25-8 as follows.

Dissolve intermediate M1 (63 g, 229 mmol) in EtOH (500 mL), NaOH (27g, 689mmol) was added, and the mixture was heated to 100 C under reflux for 5h under the protection of nitrogen. TLC monitored the reaction to completion. After cooling down, a solid was obtained by filtration and the pH was adjusted to 1 with hydrochloric acid (1N). The aqueous phase was extracted with DCM. DCM was dried over anhydrous sodium sulfate, and concentrated to give 60 g of a light yellow solid, sonicate with n-hexane (10 mL) for 5 minutes. Filtration gave 43 g of white solid product M2

According to the analysis of related databases, 875664-25-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beijing Dingcai Technology Co., Ltd.; Gao Wenzheng; Du Qian; Zhang Chunyu; Ren Xueyan; (40 pag.)CN110407822; (2019); A;,
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Application of 302912-31-8, 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. 302912-31-8, name is Ethyl 2-(4-cyanophenyl)-2-oxoacetate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Trimethylsilyl cyanide (99 muL, 0.75 mmol) was added to a solutionof ketones or aldehydes 1-6a (0.5 mmol) and the corresponding chitosan-based urea I-III (15 mg) in the proper solvent (0.5 mL) at thespecified temperature. The mixture was stirred for the time established(TLC monitoring). The catalyst was filtered and washed twice with thecorresponding solvent. To the crude reaction, 1.0 mL of a saturatedsolution of NH4Cl was added, and the mixture was extracted withEtOAc (2×5 mL). The organic phase was washed with 5.0 mL of asaturated solution of NaCl, dried with Na2SO4, and the solvents wereremoved under reduced pressure. The residue was purified by columnchromatography using 8:2 n-hexane/EtOAc for compounds 2-4b and9:1 n-hexane/EtOAc for products 5,6b, affording the corresponding Oprotectedcyanohydrins 2-4b and (R)-5,6b.300.1026; found: 300.1032.

The synthetic route of Ethyl 2-(4-cyanophenyl)-2-oxoacetate has been constantly updated, and we look forward to future research findings.

Reference:
Article; de Gonzalo, Gonzalo; Franconetti, Antonio; Fernandez, Rosario; Lassaletta, Jose M.; Cabrera-Escribano, Francisca; Carbohydrate Polymers; vol. 199; (2018); p. 365 – 374;,
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Related Products of 17417-09-3,Some common heterocyclic compound, 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, molecular formula is C7H3FN2O2, 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 5-Amino-2-fluorobenzonitrile A mixture of 5-nitro-2-fluorobenzonitrile (10 g, 60.2 mmol), Fe powder (17 g, 0.3 mol), and NH4Cl (1.7 g, 30 mmol) in EtOH/H2O (100 mL, 9:1) was heated at reflux in 2 h. The mixture was filtered at hot. The filtrate was concentrated, taken up in H2O, stirred, filtered air-dried to obtain the title solid as a tan solid, (5.0 g, 71%). 1H NMR (400 MHz, DMSO-d6): d 5.54 (s, 2H), 6.85 (m, 2H), 7.16 (t, J=8.1 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Fluoro-5-nitrobenzonitrile, its application will become more common.

Reference:
Patent; SmithKline Beecham Corporation; US6294531; (2001); B1;,
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Related Products of 61150-58-1, A common heterocyclic compound, 61150-58-1, name is 2-(2-Bromo-4-fluorophenyl)acetonitrile, molecular formula is C8H5BrFN, 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 solution of s2 in EtOH (10.0 mL) and H2O (5.0 mL) were successively added NaOH (2.94 g,73.5 mmol) and aqueous H2O2 (23 muL, 0.736 mmol) at room temperature. After the mixture washeated to reflux for 24 h, the reaction was quenched by addition of conc. HCl at 0 C. The crudemixture was extracted with EtOAc (x4) and the combined organic extracts were washed with brine,dried (Na2SO4), and concentrated in vacuo to give crude s3 (1.62 g) as pale yellow solid. Thiscrude material was used for next reaction without further purification.

The synthetic route of 61150-58-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Machida, Mizuki; Mori, Keiji; Chemistry Letters; vol. 47; 7; (2018); p. 868 – 871;,
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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. 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile

A mixture of compound 1 (0.45 g, 0.41 mmol), AcONH4 (0.13 g,1.65 mmol) and 2-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile(0.48 g, 2.47 mmol) in chloroform (30 mL) was stirredunder an atmosphere of N2 gas at 80 C overnight. The reactionmixture was then allowed to cool to room temperature. Next,dichloromethane and methanol were poured into the cooledcompound mixture for precipitation. The crude compound wasfiltered and purified by column chromatography on silica gel usingdichloromethane as the eluent to gain pure product SP-IC (2) as a red solid (0.42 g); yield 57.53%. FTIR-ATR (ZnSe, cm-1): 2894, 2220,1697, 1653, 1586, 1540, 1386; 1H NMR (CDCl3, 500 MHz, ppm):delta 8.78 (4H, s), 8.69 (4H, d, J 7.95 Hz), 8.04 (4H, d, J 7.90 Hz), 7.88(4H, d, J 6.75 Hz), 7.78e7.70 (12H, m), 7.67 (4H, s), 7.03 (4H, d,J 1.20 Hz), 2.48 (7H, t, J 7.95 Hz), 1.50-4 (8H, m), 1.19-1.07(25H, m), 0.80 (12H, t, J 7.05 Hz); 13C NMR (CDCl3,125 MHz, ppm):delta 188.18, 168.96, 160.56, 155.07, 147.36, 141.76, 141.51, 139.92, 137.98,136.87, 135.21, 134.60, 133.59, 129.87, 125.38, 124.35, 123.83, 122.86,121.46, 121.28, 114.44, 114.36, 69.90, 31.49, 30.79, 29.70, 29.08,28.70, 22.47, 14.09; UV-Vis (CHCl3) lmax/nm(epsilon/105 mol1 dm3 cm-1): 539 (1.44); Found: C, 78.18; H, 4.90; N,6.22%; molecular formula C117H88N8O4S4 requires C, 78.15; H, 4.93;N, 6.23%; Found: [MH] 1797.5803; molecular formulaC117H88N8O4S4 requires [MH] 1797.5811.

According to the analysis of related databases, 1080-74-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Park, Seo Yeon; Park, Gi Eun; Choi, Suna; Lee, Ji Hyung; Lee, Dae Hee; Cho, Min Ju; Choi, Dong Hoon; Dyes and Pigments; vol. 146; (2017); p. 226 – 233;,
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Adding a certain compound to certain chemical reactions, such as: 67832-11-5, name is 4-Bromo-2-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 67832-11-5, Computed Properties of C8H6BrN

(a) (Ss,R)-2-methyl-propane-2-sulphinic acid-[2-(5-bromo-2-cyano-phenyl)-1 – methyl-ethyl]-amide; 6.0 ml (42.8 mmol) diisopropylamine are dissolved in 80 ml THF, slowly combined with 26.7 ml (42.8 mmol) butyllithium solution (1.6 M in n-hexane) at 00C, stirred for 30 min. Then this solution is cooled to -78C and a solution of 4.0 g (20.4 mmol) 4-bromo-2-methyl-benzonithle in 15 ml THF is slowly added dropwise. This mixture is stirred for 70 minutes at -78C and then a solution of 1.5 g (10.2 mmol) (Ss)-ethylidene-N-tert.-butyl-sulphinamide (prepared analogously to J. Ellman et al. J. Org. Chem. 2001 , 66, 8772 from acetaldehyde and (Ss)-tert.-butylsulphinamide) in 15 ml THF is added dropwise. The mixture is stirred for 2.5 hours at -70 to -65C. The reaction mixture is combined with 5 ml sat. Ammonium chloride solution and after thawing it is combined with water and ethyl acetate. The aqueous phase is extracted three times with ethyl acetate, the combined organic phases are dried on sodium sulphate and evaporated to dryness in vacuo. The residue is purified by column chromatography on silica gel (eluant DCM/MeOH 100:3) Yield: 830 mg (24%) Rt value: 1.45 min (Method B) Mass spectrum: (M+H)+ = 343/345 (bromine isotope)

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2008/135524; (2008); A2;,
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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. 42872-74-2, name is 3-Bromo-4-methylbenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C8H6BrN

Dissolve 3-bromo-4-methylbenzonitrile (10g, 51mmol) in carbon tetrachloride (100mL), add NBS (22.6g, 127.5mmol) and benzoyl peroxide (272mg, 2.5mmol), and reflux 14h, the raw materials disappeared. Cool to room temperature, add water (400 mL), extract with DCM (200 mL × 2), and obtain column chromatography (P / E = 20: 1) to obtain 16.17 g of white solid with a yield of 89.6% and melting point: 48-49 C.

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; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Xu Boling; Chen Xiaoguang; Cui Guonan; Lai Fangfang; Zhou Jie; Ji Ming; Wang Xiaoyu; Du Tingting; Li Ling; Jin Jing; (144 pag.)CN110483366; (2019); A;,
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