Author: Jessica.F

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 67197-53-9 as follows. Formula: C8H5Br2N

EXAMPLE 60 6-(2,6-Dibromo-phenyl)-pyrido[2,3-d]pyrimidine-2,7-diamine To a solution of 0.23 g 60% sodium hydride suspension in 11.0 mL of 2-ethoxyethanol was added 4.18 g of 2,6-dibromophenylacetonitrile and 2.00 g of 2,4-diaminopyrimidine-5-carboxaldehyde. The reaction was refluxed for 4 hours, cooled, and poured into ice water. The residue was washed well with acetonitrile then diethyl ether to give 3.62 g of 6-(2,6-dibromo-phenyl)-pyrido[2,3-d]pyrimidine-2,7-diamine, CIMS (1% NH3 in CH4): 422=M+ +C2 H5, 396 (Base), 394=M+ +H, 393=M+; mp 284-289 C.

According to the analysis of related databases, 67197-53-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Blankley; Clifton John; Doherty; Annette Marian; Hamby; James Marino; Panek; Robert Lee; Schroeder; Mel Conrad; Showalter; Howard Daniel Hollis; Connolly; Cleo; US5733913; (1998); A;,
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These common heterocyclic compound, 1196074-43-7, name is 4-Amino-2-methoxy-5-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. COA of Formula: C8H7N3O3

A mixture of 4-amino-2-methoxy-5-nitrobenzonitrile (C-5) (5.4 g, 28 mmol, 1 ,0 eq) and tin (II) chloride (20 g, 100 mmol, 3.8 eq) in ethanol (100 ml) was heated at reflux for 3 hours. The reaction mixture was cooled, poured into water and made neutral with addition of aqueous saturated sodium bicarbonate solution. The aqueous layer was extracted with ethyl acetate (2 x 200 ml) and the combined organic extracts were dried over sodium sulfate and concentrated to yield 4,5~diamino-2-methoxybenzonitrile (C-6). ‘H NMR (400 MHz, DMSO); delta 6.62 (s, 1 H); 6.28 (s, 1 H); 5.58 (s, 2 H); 4.36 (s, 2 H); 3.70 (s, 3 H). LRMS m/z (M+H) 164.1 found, 164.1 required.

The synthetic route of 4-Amino-2-methoxy-5-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2009/140163; (2009); A1;,
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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. 872091-83-3, name is Methyl 4-chloro-3-(cyanomethyl)benzoate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of Methyl 4-chloro-3-(cyanomethyl)benzoate

Preparation 7 Methyl 4-chloro-3-(2-methoxy-2-oxoethyl)benzoateIn a 6-litre glass reactor, equipped with a reflux condenser, thermometer, pressure equalizing dropping funnel, and a mechanical stirrer was placed methyl 4-chloro-3- (cyanomethyl)benzoate (461.6 g, 2.2 mol) in methanol (759 ml, 18.7 mol). The mixture was heated to 50 0C. Chloro-trimethyl-silane (1135 ml, 9 mol) was added to this solution over 80 minutes. The mixture was refluxed for 5 hours. There was a heavy evolution of hydrogen chloride gas during this period. The mixture was left at EPO ambient temperature overnight. The solvent was evaporated. After cooling the residue was diluted with dichloromethane (1930 ml) and water (1930 ml). The mixture was stirred for 0.5 hour and the layers were separated. The aqueous phase was extracted with dichloromethane (1000 ml), that was combined with the organic layer, dried over Na2SO4, filtered and concentrated to give oil, which solidified. The residue was used in the next step without purification. (515.8 g, white crystal) Yield: 97.1 %

The synthetic route of 872091-83-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; WO2006/79857; (2006); 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. 3100-67-2, name is 1-Amino-2-naphthonitrile, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 3100-67-2

After adding nitrogen to the dry reactor 1 L 6-a 50.0 g (297 mmol), 500 mL of dimethylformamide then put the N-bromo-succinimide 55.56 g (312 mmol) slowly to the reactor. And stirred at room temperature for 4 hours. After the reaction was terminated by dropwise addition of distilled water atroom temperature, filtered, the brown crystals were separated by column chromatography to give the 6-b 68 g. (Yield 93%)

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 3100-67-2.

Reference:
Patent; SFC Co.,Ltd; Yang, Byung Son; Lee, Say Jin; Lee, Bong Hyang; Oh, Hyun Ju; Yu, Jong Ho; Hwang, Mun Chan; (67 pag.)KR2015/130797; (2015); A;,
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Reference of 175596-01-7, These common heterocyclic compound, 175596-01-7, name is Methyl 4-cyano-2-fluorobenzoate, 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 sodium hydrogensulfide hydrate (9.22 g, 0.165 mol) was added to an N,N-dimethylformamide (74 mL) suspension of methyl 4-cyano-2-fluorobenzoate () (7.37 g, 41.1 mmol) and magnesium chloride hexahydrate (10.0 g, 49.4 mmol) at room temperature. The mixture was stirred at room temperature for 4 hours. Subsequently, water (148 mL) was added to the reaction mixture, and the precipitated solid was filtered. The solid thus obtained was added to 1 N aqueous hydrochloric acid solution (148 mL), and the mixture was stirred for 20 minutes. The solid in the reaction mixture was filtered to give the title compound (7.63 g, yield: 87%). 1H-NMR (500 MHz, DMSO-d6) delta ppm: 10.21 (1H, s), 9.75 (1H, s), 7.94-7.90 (1H, m), 7.79-7.72 (2H, m), 3.88-3.87 (3H, m).

The synthetic route of 175596-01-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Company, Limited; YAMANOI, Shigeo; NAMIKI, Hidenori; OCHIAI, Yuichi; HOSHINO, Madoka; MATSUMOTO, Koji; EP2805941; (2014); A1;,
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Application of 191014-55-8,Some common heterocyclic compound, 191014-55-8, name is 4-Fluoro-2-methoxybenzonitrile, molecular formula is C8H6FNO, 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 1 g of 4-fluoro-2-methoxy-benzonitrile in 15 ml_ of dichloroethane was added 1.1 g of aluminium trichloride. The resulting mixture was refluxed for 1 day then poured slowly into water and extracted with ethyl acetate. The organic extracts were washed twice with 10% aqueous solution of sodium hydroxide. The combined basic layers were washed twice with ethyl acetate, acidified with concentrated aqueous solution of hydrochloric acid and extracted three times with ethyl acetate. The combined organic extracts were washed with water, with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 0.78 g of 4-fluoro-2- hydroxy-benzonitrile as a white solid. C7H4FNO (137.11), MS(ESI): 138.17 (M+H+).

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

Reference:
Patent; SANOFI-AVENTIS DEUTSCHLAND GMBH; WO2007/39172; (2007); A1;,
Nitrile – Wikipedia,
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Application of 53005-44-0, 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. 53005-44-0, name is 2-Methoxy-6-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 146 1-(2-methoxy-6-methylphenyl)-2-phenylethanone: To intermediate 145 (5.0 g, 34.03 mmol) in THF (50 ml), benzylmagnesium chloride (34 ml, 2M in THF, 68.02 mmol) was added at 0 C. over 30 min and heated to reflux for 15 h. The reaction mixture was cooled to room temperature, 2N HCl (200 ml) was added and again refluxed for 4 h. The reaction mixture was cooled and extracted with ethyl acetate, dried over sodium sulphate and concentrated. The crude product was column chromatographed with ethyl acetate:petroleum ether to afford to afford the title compound as brown liquid (3.7 g, 45%). 1H-NMR (delta ppm, CDCl3, 400 MHz): 7.30-7.18 (m, 6H), 6.76 (m, 2H), 4.07 (s, 2H), 3.83 (s, 3H), 2.02 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 2-Methoxy-6-methylbenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Rhizen Pharmaceuticals SA; US2012/289496; (2012); A1;,
Nitrile – Wikipedia,
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Reference of 10444-38-9, These common heterocyclic compound, 10444-38-9, name is Ethyl 4-cyanobutanoate, 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.

PREPARATION 1 Ethyl 4-(1H-tetrazole-5-yl)butanoate Ethyl 4-cyanobutyrate (approximately 15 g) was dissolved in DME. Tris(n-butyl)tin azide (5 ml) was added and the reaction solution was heated to 85 overnight then cooled to room temperature. The cooled solution was diluted with methanol (20 ml) then 1N hydrochloric acid (20 ml) was added. The solution was stirred for one hour then partitioned between ethyl acetate and water. The organic layer was separated, dried over magnesium sulfate and evaporated under reduced pressure. The residue was chromatographed by preparatory-scale HPLC (silcia column) eluted with a gradient of 30 to 70% ethyl acetate in hexane plus 1% acetic and to yield 3.39 g of the title product: n.m.r.(300 MHz, CDCl3) delta: 4.2 (q, 2H); 2.95 (t, 2H); 2.5 (t, 2H); 2.1 (t, 2H); 1.3 (t, 3H).

The synthetic route of 10444-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eli Lilly and Company; US4820723; (1989); A;,
Nitrile – Wikipedia,
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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. 6575-10-6, name is 2-Chloro-6-methoxybenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 6575-10-6

To a solution of A5.2 (334 mg, 2.0 mmol) in 10.0 mL THF was added of borane (2.0 mol/L). The mixture was heated at 90 oC for 3 h, then cooled to rt and quenched with methanol. The mixture was concentrated under vacuum, the residue was diluted with another 50 mL methanol, and then removed again. The process was repeated for four times to give the title compound (300 mg, 88%) as the crude product, which will used in next step without further purification. LC-MS: [MH]+ = 172.1

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 6575-10-6.

Reference:
Patent; NOVARTIS AG; CHAN, Ho Man; FU, Xingnian; GU, Xiang-Ju Justin; HUANG, Ying; LI, Ling; MI, Yuan; QI, Wei; SENDZIK, Martin; SUN, Yongfeng; WANG, Long; YU, Zhengtian; ZHANG, Hailong; ZHANG, Ji Yue; ZHANG, Man; ZHANG, Qiong; ZHAO, Kehao; (193 pag.)WO2017/221092; (2017); A1;,
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Electric Literature of 25978-68-1, 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 25978-68-1 as follows.

To a solution of methyl 4-cyano-3-methylbenzoate (36 mg, 0.205 mmol) in 1,4-dioxane (0.5 mL) and water (0.500 mL), was added sodium hydrogen sulfide (0.019 mL, 0.616 mmol) and triethylamine hydrochloride (170 mg, 1.233 mmol). The reaction mixture was heated at 55 0C overnight. The reaction was allowed to cool and water was added. The mixture was extracted with EtOAc. The combined organic layers were dried (Na2SC^), filtered and the solvent was evaporated in vacuo to give the product as a yellow solid. LCMS calc. = 210.1; found = 210.2 (M+l)+. 1H NMR (500 MHz, CDCl3) 7.86 (s, 1 H); 7.84 (d, J = 8.1 Hz, 1 H); 7.42 (d, J= 7.9 Hz, 1 H); 7.16 (s, 2 H); 3.93 (s, 3 H); 2.51 (s, 3 H).

According to the analysis of related databases, 25978-68-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2007/79186; (2007); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts