Author: Jessica.F

Electric Literature of 29509-06-6, A common heterocyclic compound, 29509-06-6, name is 4-Methyl-3-oxopentanenitrile, molecular formula is C6H9NO, 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.

Hydroxylamine hydrochloride (10.3 g, 148 mmol) was slowly added to an ice cold solution of NaOH (25.9 g, 645 mmol) in water (73 mL) and the resulting solution was poured into a solution of crude 3-oxo-4-methylpentanenitrile while stirring. The resulting yellow solution was heated at 50 C for 2.5 hours to produce a less dense yellow oil. The warm reaction mixture was immediately extracted with CHCl3 (3 x 100 mL) without cooling. The combined organic layers were dried (MgSO4), and concentrated in vacuo. The resulting oily yellow solid was filtered through a pad of silica (10% acetone/90% CH2Cl2) to afford the desired isoxazole as a yellow solid (11.3 g, 70%): mp 63-65 C; TLC Rf (5% acetone/95% CH2Cl2) 0.19; 1H-NMR (DMSO-d6) d 1.12 (d, J=7.0 Hz, 6H), 2.72 (sept,J=7.0 Hz, 1H), 4.80 (s, 2H), 6.44 (s, 1H); FAB-MS m/z (rel abundance) 127 ((M+H)+; 67%).

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; Bayer Pharmaceuticals Corp.; EP1047418; (2005); B1;,
Nitrile – Wikipedia,
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Reference of 1194-02-1, The chemical industry reduces the impact on the environment during synthesis 1194-02-1, name is 4-Fluorobenzonitrile, I believe this compound will play a more active role in future production and life.

Preparation of BB8: 4-Fluoro-N-hydroxy-benzamidine; To a solution of the 4-fluoro-benzonitrile (10.0 g, 52.9 mmol) in ethanol (200 mL), the solution of NH2OH-HCl (4.0 g, 58.2 mmmol) in H20 (4 mL) was added dropwise. The mixture was stirred vigorously at about 65 C and stood overnight. The analysis by TLC indicated the complete consumption of starting material. The solution was concentrated to remove the solvent. The residue was dissolved in DCM and washed with water, brine, dried over Na2S04 and concentrated in vacuum to afford 4-Fluoro-N-hydroxy-benzamidine as pale- yellow solid (BB8).

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-Fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; CUSACK, Kevin, P.; BREINLINGER, Eric, C.; FIX-STENZEL, Shannon, R.; STOFFEL, Robert, H.; WOLLER, Kevin, R.; WO2011/71570; (2011); A1;,
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Electric Literature of 4426-11-3, 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. 4426-11-3, name is Cyclobutanecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

LiHMDS (1M in toluene, 17.7 mL, 17.7 mmol, 3.1 eq) is added dropwise to a cold (-5 C.) solution of 4-bromo-2-fluoro-pyridine [Marsais, F. et al, Journal of Organic Chemistry, (1992), 57, 565-573] (1 g, 5.7 mmol) and cyclobutanecarbonitrile (1.39 g, 17.1 mmol, 3 eq) in toluene (20 mL). The reaction mixture is allowed to warm to rt, stirred for 5 h, quenched by addition of a saturated solution of NaHCO3 and filtered through a pad of celite. The filtrate is extracted with EtOAc. The organic phase is washed with a saturated solution of NaHCO3, dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (Hex/EtOAc, 1:0?95:5) to afford 933 mg of the title compound as a yellow oil: ESI-MS: 237.0/239.0 [M+H]+; tR=4.27 min (System 1); TLC: Rf’0.30 (Hex/EtOAc, 9:1).

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

Reference:
Patent; Novartis AG; US2009/163469; (2009); A1;,
Nitrile – Wikipedia,
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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. 326-62-5 name is 2-(2-Fluorophenyl)acetonitrile, 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. 326-62-5

General procedure: A solution of aryl acetonitrile 2 (50 mg), and triethylamine (1.1 equiv.) in dimethylformamide dimethyl acetal (0.5 mL, 3.76 mmol) was heated in a microwave reactor at 120 C for 20 minutes. The mixture was cooled to RT, and solvents were then evaporated. To the resulting crude product 3 was added hydrazine mono-hydrobromide (3.0 equiv.), 200 proof EtOH (1.0 mL), and H2O (0.3 mL). The mixture was heated in a microwave reactor at 120 C for 20 minutes. The mixture was cooled to RT and concentrated in vacuo. The resulting residue was subjected to liquid-liquid extraction using saturated NaHCO3 (aq) and CH2Cl2. The organic layer was collected, dried over anhydrous MgSO4, filtered and removed under vacuum to afford 4.The resulting crude product 4 and 2-arylsubstitutedmalondialdehydes or 1,1,3,3tetramethoxypropane (1.0 equiv.) were dissolved in glacial AcOH (1.0 mL) and 200 proof EtOH (1.5 mL). The mixture was heated in a microwave reactor at 120 C for 20 minutes. After cooling on ice, the precipitate was collected on a fine scintered-glass frit and washed with icecold EtOH (2 x 1.0 mL). The resulting crystals 5-32 were dried and collected.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(2-Fluorophenyl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Article; Singleton, Justin D.; Dass, Reuben; Neubert, Nathaniel R.; Smith, Rachel M.; Webber, Zak; Hansen, Marc D.H.; Peterson, Matt A.; Bioorganic and Medicinal Chemistry Letters; vol. 30; 2; (2020);,
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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. 3759-28-2, name is 2-(Cyanomethyl)benzonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C9H6N2

Step B 4-Cyano-N-(1,1-dimethylethoxy)carbonyl-4-(2-cyanophenyl)piperidine A solution of bis(2-chloroethyl)-N-(1,1-dimethylethoxy)carbonyl amine (19 g, 78 mmol) and homophthalonitrile (8.6 g, 60 mmol) and cesium carbonate (79 g, 241 mmol) was stirred at 60 C. for 12 hours. The solution cooled to room temperature and diluted with 500 ml EtOAc and washed with saturated aqueous NaHSO4 and saturated aqueous NaCl. The solution was dried over Na2SO4, concentrated in vacuo, and purified by PCTLC (30% EtOAc in Hexane) to afforded 4-cyano-N-(1,1-dimethylethoxy)carbonyl-4-(2-cyanophenyl) piperidine as a yellow/orange oil. 1H NMR (CDCl3): delta7.81-7.79 (d, 2H), 7.67-7.65 (m, 2H), 7.51-7.47 (m, 1H), 4.31 (br s, 2H), 3.26 (br s, 2H), 2.33-2.20 (m, 4H), 1.48 (s, 9H).

The synthetic route of 3759-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US6319932; (2001); B1;,
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Adding a certain compound to certain chemical reactions, such as: 67515-59-7, name is 4-Fluoro-3-(trifluoromethyl)benzonitrile, 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 67515-59-7, category: nitriles-buliding-blocks

4-fluoro-3-(trifluoromethyl)benzonitrile (1 g; 5.29 mmol; 1 eq.) and (R)-(-)-2-methylpiperidine (3.1 rmL; 26.4 mmol; 5 eq.) in DMSO (10 mL) were heated at 1000C under nitrogen for 12h. The reaction mixture was then diluted in EtOAc, washed with water, NaHCO3 sat and NH4CI sat. The organic phase was dried over MgSO4, filtered and evaporated under vacuum to give a yellow oil, that was submitted to the next step without further purification. HPLC (Method A) Rt 5.65 min. LC/MS (Method B): 269.1 (M+H)+.

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-Fluoro-3-(trifluoromethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SERONO S.A.; MUZERELLE, Mathilde; QUATTROPANI, Anna; MONTAGNE, Cyril; DORBAIS, Jerome; WO2010/69949; (2010); A1;,
Nitrile – Wikipedia,
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Electric Literature of 138642-47-4, These common heterocyclic compound, 138642-47-4, name is 2-Bromo-5-methoxybenzonitrile, 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: To a mixture of substituted alcohol 1 (1 mmol) and substituted nitrile 2 (1 mmol), T3P 50 wt% in ethyl acetate (50 mol%) was added and stirred at 90 C. After the reactant disappeared (monitored by TLC), the reaction mixture was cooled to room temperature, excess of water was added and extracted with ethyl acetate and combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by recrystallization using DCM: pet ether (1:9) mixture to get pure compound 3.

The synthetic route of 138642-47-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chaithra, Nagaraju; Mantelingu, Kempegowda; Rangappa, Kanchugarakoppal S.; Rangappa, Shobith; Sandhya, Nagarakere C.; Swarup, Hassan A.; Synthetic Communications; vol. 49; 16; (2019); p. 2106 – 2116;,
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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. 7357-70-2, name is 2-Cyanothioacetamide, A new synthetic method of this compound is introduced below., Recommanded Product: 7357-70-2

12.46 g (75 mmol) of 4-(2-hydroxyethoxy)benzaldehyde, 15.02 g (150 mmol) of cyanothioacetamide and 15.15 g (150 mmol) of N-methylmorpholine are initially charged in 75 ml of ethanol and heated under reflux for 3 h. After cooling, the reaction solution is concentrated under reduced pressure. The residue is dissolved in IN aqueous sodium hydroxide solution and washed twice with ethyl acetate. The aqueous sodium hydroxide phase is acidified with IN hydrochloric acid and the precipitated crystals are filtered off with suction and dried under reduced pressure at 450C. This gives 12.05 g (51% of theory) of product.MS (ESIpos): m/z = 313 (M+H)+, 330 (M+NH^1H=NMR (300 MHz, DMSO-d*): delta = 3.7 (t, 2H); 4.1 (t, 2H); 7.1 (d, 2H); 7.4 (d, 2H); 8.0 (br s, 2H).

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; BAYER HEALTHCARE AG; WO2007/73855; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 64248-62-0,Some common heterocyclic compound, 64248-62-0, name is 3,4-Difluorobenzonitrile, molecular formula is C7H3F2N, 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.

Step 1: 3,4-Difluorobenzonitrile (30 g, 0 · 22 mol) was placed in a 500 mL autoclave, and an ammonia gas of 37 · 4 g (2.2 mol) was introduced. Then, the temperature was raised to 110 C for 24 hours, sampled, and the reaction was monitored by liquid chromatography to a normalized content of 0.5%. After cooling to room temperature, pressure was added, toluene (120 mL) was added, the temperature was raised to 60 C for 0.5 h, then the temperature was lowered to 0 C, filtered, and the filter cake was mixed with water (150 mL X 3 ), filtered, and filtered cake 40. (: Vacuum drying to give 2- fluoro-4-aminobenzonitrile 27.9 g (yield 95%; purity >99%, off-white solid, melting point 70-72 C). It is 3-fluoro-4-aminobenzonitrile.

The synthetic route of 64248-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jinkai (Liaoning) Chemical Co., Ltd.; Yang Xiaoge; Wang Yongcan; Wang Xiuying; Jiang Zhipeng; Zhang Jinxin; Song Tongji; (13 pag.)CN109678741; (2019); A;,
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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 52798-01-3 as follows. Computed Properties of C10H9NO2

To a solution of methyl (4-cyanophenyl)acetate (4.00 g, 27.8 mmol) in MeOH (20 mL), hydroxylamine hydrochloride (3.17 g, 45.7 mmol) and NaHCO3 (3.84 g, 45.7 mmol) is added. The suspension is stirred at 60 C. for 18 h before it is filtered and the filtrate is concentrated. The residue is dissolved in DCM, washed with water followed by brine, dried over MgSO4, filtered, concentrated and dried to give methyl [4-(N-hydroxycarbamimidoyl)-phenyl]-acetate (3.67 g) as a colourless oil; LC-MS: tR=0.50 min, [M+1]+=209.05.

According to the analysis of related databases, 52798-01-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Actelion Pharmaceuticals Ltd.; US2010/63108; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts