Author: tianli

10406-25-4,Some common heterocyclic compound, 10406-25-4, name is 4-(Aminomethyl)benzonitrile, molecular formula is C8H8N2, 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 87 Preparation of 4-(aminomethyl)phenyl-N-hydroxyamidine (4-4) Hydroxylamine hydrochloride (7 g) was added to a solution of compound 4-3 (7 g) and NMM (4 ml) in methanol (100 ml). The mixture was stirred at ambient temperature for 3 days. The compound was purified by RP HPLC to give the title compound (7 g, 89%). MS (electrospray): 166 (M+1).

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

Reference:
Patent; Corvas International, Inc.; US2002/37857; (2002); A1;; ; Patent; Corvas International, Inc.; US6586405; (2003); B2;,
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42872-74-2, 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. 42872-74-2, name is 3-Bromo-4-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

[0152] To a solution of 2 (300 mg, 137 mmol) in toluene (15 mL) was added 3- bromo-4-methylbenzonitrile (402 mg, 2.05 mmol), racemic-2,2′-bis(diphenylphosphino)-l,l’- binaphthyl (170 mg, 0.27 mmoi) and cesium carbonate (892 mg, 2.74 mmol). The mixture was purged with nitrogen for 10 min. Tris(dibenzylideneacetone)dipaliadium(O) (125 mg, 0.14 mmoi) was added and the mixture was heated to 110 C for 16 h, then diluted with ethyl acetate (20 mL) and filtered through celite. The solution was concentrated in vacuo, the residue was purified by chromatography (silica gei, 0-15% ethyl acetate/methylene chloride) to afford Example 61 as a light yellow solid (111 mg, 24%): 1H NMR (300 MHz, DMSO-d6) delta 7.76 (d, J = 2.1 Hz, 1H), 7.74-7.73 (m, 3H), 7.27 (s, 1H), 7.06 (d, J = 2.1 Hz, 1H), 3.96 (s, 3H), 2.37 (s, 3H), 2.28 (s, 3H), 2.18 (s, 3H); ESI m/z 335 [M + H)

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:
Patent; ZENITH EPIGENETICS CORP.; JIANG, May, Xiaowu; MOLINO, Bruce, Francis; LIU, Shuang; WANG, Ruifang; DUFFY, Bryan, Cordell; QUINN, John, Frederick; WAGNER, Gregory, Steven; (114 pag.)WO2016/87942; (2016); A1;,
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10406-25-4, 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. 10406-25-4, name is 4-(Aminomethyl)benzonitrile, A new synthetic method of this compound is introduced below.

Biphenyl-3 -carboxylic acid (500mg, 2. 52mmol) and 4-aminomethyl-benzonitrile (425mg, 2.S2mmol) were suspended in DCM (25mL) and DIPEA (873uL, 5.O4mmol), EDC (484mg, 2.S2mmol) and HOBt (3 86mg, 2.S2mmol) were added. The reactionmixture was stirred overnight, concentrated in vacuo and partitioned between EtOAc (lOOmL) and water (lOOmL). The organic fraction was washed with water (lOOmL), sat aq NaHCO3 (5OmL), brine (5OmL), dried (MgSO4) and concentrated in vacuo to give the title compound (738mg, 94%) as a brown solid. LCMS: ES 313.0 [IVIHf.

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; PROXIMAGEN LIMITED; MEO, Paul; STEWART, Alison; HOBBS, Christopher; WO2014/20351; (2014); 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. 50670-64-9, name is 5-Amino-2-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., 50670-64-9

Example 22 5-Bromo-2-methylbenzonitrileWater (13.5 mL), HBr (74%, 14.4 mL) and 5-amino-2-methylbenzonitrile (2.0 g, 15.1 mmol) dissolved in water (24 mL) was added to a flask and heated to 50 C for for 20 min. Then the mixture was cooled to 0-5 0C, and a solution OfNaNO2 (1.2 g, 17.4 mmol) in water was added. The reaction mixture was stirred for 10 min at 0-5 C, then was warmed to 40 C. A solution of CuBr (6.5 g, 45.1 mmol) in water (36 mL) and HBr (7.2 mL) was added to the mixture, and refluxed for 2 h. The mixture was extracted with AcOEt, and the organic layer was washed by saturated NaHCtheta3 solution and brine, and dried over Na2SOphi The crude product was purified by flask chomatograph (PE:EA=50: 1), obtaining 2.3 g of 5-bromo-2-methylbenzonitrile as a white solid (yield: 77%). 1H NMR (400 MHz, CDCl3) delta 7.72 (s, 1 H), 7.59 (d, J=8.0 Hz, 1 H), 7.19 (d, J=8.0 Hz, 1 H), 2.51 (s, 3 H).

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:
Patent; GLAXO GROUP LIMITED; WO2009/100169; (2009); A1;,
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52133-67-2, 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. 52133-67-2, name is Ethyl 2-cyano-4,4-diethoxybutyrate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Method AJ: 2-(Pyridin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-ol (xliii) To a solution of nicotinimidamide (5.03 g, 41.6 mmol, 1.2 eq.) in EtOH (100 mL), was added NaOMe (4.8 g, 88.8 mmol, 2.5 eq.). The mixture was stirred at room temperature for 4 h. The reaction mixture was added to ethyl 2-cyano-4,4-diethoxybutanoate (8.00 g, 34.9 mmol, 1 eq.). This mixture was stirred at 105¡ã C. overnight. After cooling, the reaction mixture was acidified with conc. HCl and stirred at room temperature for 2 h. A precipitate formed and was collected and washed with H2O (20 mL*2). After lyophilization, 3.10 g of product was obtained as a gray yellow solid (yield 41.8percent). LCMS m/z=213.1 (M+1) (Method B) (retention time=1.07 min). 1H NMR (400 MHz, DMSO-d6): delta 12.26 (s, 1H), 12.04 (s, 1H), 9.23 (d, J=1.6 Hz, 1H), 8.70 (dd, J=4.8, 1.2 Hz, 1H), 8.43-8.40 (m, 1H), 7.55 (dd, J=8.0, 4.8 Hz, 1H), 7.12 (d, J=1.6 Hz, 1H), 6.51 (d, J=2.8 Hz, 1H).

The synthetic route of Ethyl 2-cyano-4,4-diethoxybutyrate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Suzuki, Masaki; Kondo, Kazumi; Kurimura, Muneaki; Valluru, Krishna Reddy; Takahashi, Akira; Kuroda, Takeshi; Takahashi, Haruka; Fukushima, Tae; Miyamura, Shin; Ghosh, Indranath; Dogra, Abhishek; Harriman, Geraldine; Elder, Amy; Shimizu, Satoshi; Hodgetts, Kevin J.; Newcom, Jason S.; US2015/307477; (2015); A1;,
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218632-01-0, A common heterocyclic compound, 218632-01-0, name is 3-Fluoro-4-nitrobenzonitrile, molecular formula is C7H3FN2O2, 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 3-fluoro-4-nitrobenzonitrile (5.0 g, 0.030 mmol) in MeOH (50 mL) were added iron powder (5 g) and conc.HC1 (20 mL). The reaction mass was stirred at RT for 2 h. The reaction mass was filtered. The filtrate was concentrated and then diluted with water, extracted with EtOAc and basified with 10% NaHCO3 solution. The organic portion wasdried over Na2504 and concentrated to afford 4.5 g of the title product.?H NMR (300 MHz,DMSO-d6): 7.52-7.48 (d, J= 11.7 Hz, 1H), 7.31-7.29 (d, J= 8.1 Hz, 1H), 6.82.-6.76 (d, J=8.7 Hz, 1H), 6.24 (s, 2H).

The synthetic route of 218632-01-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; MUTHUKAMAN, Nagarajan; PISAL, Dnyandeo; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; KADAM, Sheetal R; (303 pag.)WO2016/55947; (2016); A1;,
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151-18-8, The chemical industry reduces the impact on the environment during synthesis 151-18-8, name is 3-Aminopropanenitrile, I believe this compound will play a more active role in future production and life.

A solution of 6, 7-DIMETHOXY-L- (3-METHOXY-BENZOYL)-ISOQUINOLINE-4-CARBOXYLIC acid (170 mg, 0.46 mmol) in dry, N, N-dimethylformamide (5 ML) was chilled in an ice bath under argon. With stirring, triethylamine (97 uL, 0.69 mmol) and isobutylchloroformate (72 uL, 0.56 uL) were added. The solution was stirred for 30 min and then 3-aminopropionitrile fumarate (118 mg, 0.92 mmol) and triethylamine (250 uL, 1.79 mmol) were added. The solution was allowed to warmed to room temperature with stirring overnight. The reaction mixture was poured into a 2% aqueous sodium bicarbonate solution (50 mL) and extracted with ethyl acetate (3 x 25 mL). The combined ethyl acetate layers were dried over magnesium sulfate, filtered and concentrated III VACUO to afford 107 mg (55%) of an off white solid and used without further purification: APCI-MS M/E calcd for C23H2LN3O5 (M-H+) 420.4, found 420.0 ; 1H NMR (300 MHz) compatible.

The chemical industry reduces the impact on the environment during synthesis 3-Aminopropanenitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2004/101528; (2004); A2;,
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1080-74-6, Adding some certain compound to certain chemical reactions, such as: 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, 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 1080-74-6.

To a degassed solution of intermediate 49 (250 mg, 0.19 mmol) in a mixture of pyridine (2 cm3) and chloroform (18 cm3) at 0 C is added 2-(3- oxo-indan-1 -ylidene)-malononitrile (1 12 mg, 0.58 mmol) is added and the mixture stirred at 0 C for 3 hours. The reaction is quenched by addition of aqueous hydrochloric acid solution (10 cm3, 2 M) and the aqueous layer extracted with dichloromethane (20 cm3). The combined organic layer is washed with brine (50 cm3), dried over anhydrous magnesium sulphate, filtered and the solvent removed in vacuo. This residue is purified by column chromatography using a graded solvent system (40-60 petrol:dichloromethane; 3:2 to 3:7). The solid is triturated in ice-cooled acetone (30 cm3) and with diethylether (20 cm3) to give compound 104 (135 mg, 42%) as a blue solid. 1H NMR (400 MHz, CD2CI2) 8.85 (2H, s), 8.67 (2H, d, J 7.5), 8.24 (2H, s), 7.95 (4H, t, J 9.2), 7.75 – 7.83 (4H, m), 7.59 (2H, d, J 8.3), 7.23 (8H, d, J 8.4), 6.83 (8H, d, J 8.4), 3.87 (8H, t, J 6.6), 1 .63 – 1 .74 (8H, m), 1 .31 – 1 .39 (8H, m), 1 .18 – 1 .31 (32H, m), 0.82 (12H, t, J 7.0).

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 1080-74-6.

Reference:
Patent; MERCK PATENT GMBH; MORSE, Graham; NANSON, Lana; MITCHELL, William; KROMPIEC, Michal; D’LAVARI, Mansoor; PRON, Agnieszka; (327 pag.)WO2018/65350; (2018); A1;,
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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. 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, A new synthetic method of this compound is introduced below., 1080-74-6

A solution of compound 2 (0.28 mmol, 50 mg) in ethanol (5 mL) was added 2-(1,2-dihydro-1-oxoinden-3-ylidene)malononitrile (0.28 mmol, 54 mg) and the mixture was stirred for 4 days at room temperature. The precipitate obtained was filtered and the product was recrystallized from ethanol which gave the pure compound 3c. 2-(((2-(1H-Pyrrol-1-yl)thiazol-5-yl)methylene)-1,2-dihydro-1- oxoinden-3-ylidene)malononitrile 3c. Orange solid (75 mg, 87%). Mp 294-295 C. 1H NMR (CDCl3) delta 6.43-6.45 (m, 2H, 3”-H and 4”-H), 7.50-7.51 (m, 2H, 2”-H and 5”-H), 7.80-7.85 (m, 2H, 4-H and 7-H), 7.96 (dd, 1H, J 6.8 and J 0.6 Hz, 6-H), 8.19 (s, 1H, 40-H), 8.74 (dd, 1H, J 6.8 and J 0.6 Hz, 5-H), 8.87 (s, 1H, C=CH). 13C NMR (CDCl3) delta108.2, 112.4, 114.1, 114.2, 120.1, 122.5, 123.0, 124.1, 125.6, 127.4, 134.9, 135.8, 135.9, 136.7, 140.1, 158.5, 159.5, 170.4. lambdamax (dioxane)/ nm 465 ( 3/dm3 mol-1 cm-1 36,130). IR (CHCl3): 2224, 1700, 1590, 1571,1554,1503,1398,1307,1290,1275,1253,1226,1189,1044, 988, 919 cm-1. MS (EI) m/z (%) 354 ([M], 87), 2891 (19), 288 (100), 263 (10), 262 (50), 234 (24), 218 (10), 207 (11), 189 (17), 164 (15), 163 (61); HMRS: m/z (EI) for C20H10N4OS: calcd 354.0575; found: 354.0570.

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; Castro, M. Cidalia R.; Belsley; Raposo, M. Manuela M.; Dyes and Pigments; vol. 128; (2016); p. 89 – 95;,
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31643-49-9, Name is 4-Nitrophthalonitrile, 31643-49-9, 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.

This synthesis is a modified version of the method described previously [24] and [25]. 4-Nitrophthalonitrile (8.7 g, 50 mmol) and an excess of 3-hydroxypyridine (1) (7.13 g, 75 mmol) were dissolved in 100 mL of dry DMSO under inert gas. A portion of dry potassium carbonate (13.8 g, 100 mmol) was added. After 48 h stirring at room temperature next portion of potassium carbonate was added (10 g, 72 mmol). After 72 h the mixture was poured to 500 mL of water. Precipitate was washed thoroughly with water. The isolated and dried product was dissolved in hot ethanol and active charcoal was added. After filtration ethanol solution was poured into water. Precipitate was filtered, washed with water and dried. Chromatography on silica gel with CH2Cl2 afforded solid product that was dissolved in Ac and slowly poured to water. The white crystals of high purity were obtained. Yield 8.73 g (80%). M = 221.22 g mol-1, C13H7N3O. IR (KBr): nu, cm-1 = 3107, 3070, 3039, 2228 (CN), 1596, 1574, 1566, 1487, 1424, 1314, 1280 (Ar-O-Ar), 1253 (Ar-O-Ar), 1216, 1084, 1025, 956, 892, 854, 820, 706, 615, 527. 1H NMR (200 MHz, DMSO-d6): delta = 8.52 (m, 1H), 8.40 (s, 1H), 8.12 (d, 1H), 7.9 (dd, 1H), 7.71 (m, 1H), 7.54 (m, 1H), 7.49 (dd, 1H). EI-MS (200 C, 70 eV): m/z 221 [M]+, 127 [M+ – C5H4NO], 78 [C5H4N]+.

Statistics shows that 4-Nitrophthalonitrile is playing an increasingly important role. we look forward to future research findings about 31643-49-9.

Reference:
Article; Mantareva, Vanya; Angelov, Ivan; Kussovski, Veselin; Dimitrov, Roumen; Lapok, Lukasz; Woehrle, Dieter; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 4430 – 4440;,
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