Month: May 2021

Some common heterocyclic compound, 89942-45-0, name is 2-(Hydroxymethyl)benzonitrile, molecular formula is C8H7NO, 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. Application In Synthesis of 2-(Hydroxymethyl)benzonitrile

General procedure: A mixture of p-methylbenzyl alcohol (1.0 mmol), N-phenylglycine(0.0076 g, 0.05 mmol), CuBr2 (0.0112 g, 0.05 mmol),Na2CO3 (0.1060 g, 1.0 mmol), TEMPO (0.0078 g, 0.05 mmol),H2O (3.0 mL) were added to a 100 mL Schlenk tube, which wasvigorously stirred in air under reflux for 0.5 h. After the reaction,the product was extracted with CH2Cl2 (3 × 2.0 mL). Thecombined organic phase was washed with H2O (3.0 mL) anddried over anhydrous MgSO4. After concentration undervacuum, the residue was purified by column chromatography toafford p-methylbenzaldehyde.Isolated yield: 0.1080 g (90%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 89942-45-0, its application will become more common.

Reference:
Article; Zhang, Guofu; Lei, Jie; Han, Xingwang; Luan, Yuxin; Ding, Chengrong; Shan, Shang; Synlett; vol. 26; 6; (2015); p. 779 – 784;,
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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. 24056-34-6, name is 4-Hydroxycyclohexanecarbonitrile, A new synthetic method of this compound is introduced below., category: nitriles-buliding-blocks

Into a 1-L 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 119.2 (10 g, 79.89 mmol, 3.00 equiv), FeCl3 (435 mg, 0.10 equiv). 119.3 (4.5 g, 26.76 mmol, 1.00 equiv) was added to the solution below 10 C. The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 50 ml of water. The resulting solution was extracted with 2×500 mL of ethyl acetate and the organic layers combined and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5). This resulted in 2 g (25%) of 119.4 as colorless oil.

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; Gilead Apollo, LLC; Ghosh, Shomir; Greenwood, Jeremy Robert; Harriman, Geraldine C.; Leit De Moradei, Silvana Marcel; (290 pag.)US2017/166584; (2017); 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. 6476-32-0, name is 2-Phenoxybenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 6476-32-0

To a solution of compound B2 (1.00 g, 5.12 mmol) in MeOH (30 mL) was added Raney-Ni (43.9 mg, 0.512 mmol) and NH3.H20 (3 mL), the reaction mixture was stirred under H2 balloon (15 psi) at l5C for 16 hours to give a black suspension. TLC showed the reaction was complete. The reaction mixture was filtered, the filtrate was concentrated under reduced pressure to remove MeOH. The residue was diluted with DCM (20 mL), dried over anhydrous Na2S04, filtered and concentrated under reduce pressure to give compound B3 (820 mg) as a yellow oil.

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 6476-32-0.

Reference:
Patent; QURIENT CO., LTD.; LEAD DISCOVERY CENTER GMBH; NAM, Kiyean; KIM, Jaeseung; JEON, Yeejin; YU, Donghoon; SEO, Mooyoung; PARK, Dongsik; EICKHOFF, Jan; ZISCHINSKY, Gunther; (217 pag.)WO2019/197549; (2019); A1;,
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262298-02-2, name is 4-Methoxy-2-methylphenylacetonitrile, 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. Safety of 4-Methoxy-2-methylphenylacetonitrile

Under anhydrous conditions, (4-methoxy-2-methylphenyl)acetonitrile(25.0 kg, 155 moles, available commercially) and 68.3 kg of ethyl acetate were mixed to obtain a solution. The resulting solution was heated to 35 C and potassium ^-butoxide in THF (100 kg, 20 wt %, 178 moles) was added over a 30 to 60 minute period controlling the temperature at 35 C. Following the addition, the reaction mass was heated to 45 C and held for 60 minutes. At the end of the hold period, a sample was analyzed by HPLC. The reaction mixture was then cooled to 25 C and combined with 3 other batches for a total of 843 kg of solution.

The synthetic route of 262298-02-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB PHARMA COMPANY; WO2005/51954; (2005); A2;,
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Electric Literature of 180976-09-4,Some common heterocyclic compound, 180976-09-4, name is tert-Butyl (cyanomethyl)(methyl)carbamate, molecular formula is C8H14N2O2, 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 solution of cyanomethyl-methyl-carbamic acid tert-butyl ester (6.01 g, 35.3 mmol) and hydroxylamine (5.13 g, 77.6 mmol, 50percent solution in water) in ethanol (30 mL) was heated at reflux for 1 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was azeotroped twice with ethanol, then once with isopropyl alcohol to afford a white solid. This was triturated with ether and collected by filtration, then dried under vacuum at room temperature to afford the title compound (5.27 g) as a white solid. A further crop could be obtained from the mother liquors by the same work-up procedure. Total yield 6.93 g (96percent). 1H NMR (CDCI3): 1.48 (S, 9 H), 2.87 (s, 3 H), 3.84 (s, 2 H), 4.73 (brs., 1 H), 5.09 (bra., 2 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl (cyanomethyl)(methyl)carbamate, its application will become more common.

Reference:
Patent; ARGENTA DISCOVERY LIMITED; ASTRAZENECA AB; WO2008/23157; (2008); A1;,
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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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