Month: March 2021

13388-75-5, name is 2-(3,5-Dimethoxyphenyl)acetonitrile, 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. Application In Synthesis of 2-(3,5-Dimethoxyphenyl)acetonitrile

A mixture of 3,5-dimethoxyphenyl acetonitrile (10 g, 56.43 mmol) and methyl iodide (10.5 mL) in anhydrous DMF (280 mL) under an argon atmosphere was added dropwise (via cannula) to a solution of sodium hydride (4.06 g, 169.20 mmol) in 30 mL DMF at 0C. The mixture was warmed to room temperature and stirred for 1.5 hours. Upon completion, the reaction mixture was quenched by the addition of saturated aqueous NH4C1 and diluted with diethyl ether. The organic layer was separated and the aqueous phase was extracted with diethyl ether. The combined organic layer was washed with brine and dried (MgS04) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel (10-30% ethyl acetate in hexanes) to afford 11.3 g (98% yield) of compound 6 as a viscous oil. 1H NMR (500 MHz, CDC13) delta 6.61 (d, J= 2.0 Hz, 2H, 2-H, 6-H, ArH), 6.27 (t, J= 2.0 Hz, 1H, 4-H, ArH), 3.81 (s, 6H, OMe), 1.70 (s, 6H, C(C)2C).

The synthetic route of 13388-75-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NORTHEASTERN UNIVERSITY; MAKRIYANNIS, Alexandros; D’SOUZA, Marsha, R.; BAJAJ, Shama; NIKAS, Spyridon, P.; THAKUR, Ganeshsingh, A.; WO2014/62965; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 52805-37-5, name is 3-(Benzyloxy)-4-methoxybenzonitrile, 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 52805-37-5, Recommanded Product: 3-(Benzyloxy)-4-methoxybenzonitrile

A solution of 3-benzyloxy-4-methoxybenzonitrile 3 (0.81 g, 3.38 mmol) in glacial acetic acid (3.2 mL) was added dropwise to concentrated nitric acid (70 %, 8 mL) with cooling in ice-bath. Once the addition was complete, the reaction was stirred for a further 1 h, after which time the mixture was poured into water. The resulting precipitate was isolated by filtration and washed with water to afford the solid. The solid was dissolved in dichloromethane. The solution was washed with water, dried (Na2SO4), and evaporated to give a product 4 (0.70 g, 2.46 mmol) in 73% yield. 1H NMR (400 MHz, CDCl3, delta): 7.80 (s, 1H), 7.46-7.36 (m, 5H), 7.23 (s, 1H), 5.25 (s, 2H), 4.03 (s, 3H); 13C NMR (100.6 MHz, CDCl3, delta): 152.6, 152.4, 142.8, 134.3, 129.0, 128.9, 127.4, 117.0, 115.5, 108.1, 100.6, 71.7, 56.8; IR (KBr): 2223, 1567, 1529, 1340, 1295, 750, 696 cm-1; MS m/z: 285.0 (M+1, 25.4), 154.0 (100.0), 136.0 (85.6), 107.0 (39.6), 91.0 (67.3), 77.0 (47.9); HRMS-FAB (m/z): [M+1]+ calcd for C15H13N2O4, 285.0875; found, 285.0870.

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

Reference:
Article; Yin, Kai-Hao; Hsieh, Yi-Han; Sulake, Rohidas S.; Wang, Su-Pei; Chao, Jui-I.; Chen, Chinpiao; Bioorganic and Medicinal Chemistry Letters; vol. 24; 22; (2014); p. 5247 – 5250;,
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Related Products of 1009-35-4, The chemical industry reduces the impact on the environment during synthesis 1009-35-4, name is 4-Fluoro-3-nitrobenzonitrile, I believe this compound will play a more active role in future production and life.

Step l:4-(2-Hydroxy-ethoxy)-3-nitro-benzonitrile (3_28_2) [00222] Sodium (1.038 g, 45.2 mmol) was added to a mixture of ethylene glycol (28.03 g, 0.451 mol) in tetrahydrofuran (20 mL) at room temperature. After all sodium was consumed, 4-fluoro-3-nitro-benzonitrile 3_28_1 (5.0 g, 30.1 mmol) in tetrahydrofuran (10 mL) was added at -10¡ãC and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was quenched by adding ice- water and neutralized to pH 7 using dilute hydrochloric acid at 0¡ãC. The mixture was extracted with ethyl acetate and the extract was washed with brine, dried over sodium sulfate and concentrated to dryness. The residue was purified by crystallization from ethyl acetate/hexanes to give the desired product (4.45 g, 71 percent yield) as a light yellow solid. [00223] NM (400 MHz, DMSO-d6): delta = 3.60-3.79 (m, 2H), 4.17-4.37 (m, 2H), 4.94 (t, J = 5.3 Hz, 1H), 7.56 (d, J = 8.8 Hz, 1H), 8.09 (dd, J = 8.9, 2.2 Hz, 1H), 8.45 (d, J = 2.0 Hz, 1H). [00224] MS (ES ) m/z: [M-H]’ calcd for C9H7N2O4: 207.18. Found: 206.90.

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

Reference:
Patent; AICURIS GMBH & CO. KG; KLENKE, Burkhard; WIEGAND, Irith; SCHIFFER, Guido; BROETZ-OESTERHELT, Heike; MAITI, Samarendra N.; KHAN, Jehangir; REDDY, Andhe; YANG, Zhixiang; HENA, Mostafa; JIA, Guofeng; LIGONG, Ou; LIANG, Hong; YIP, Judy; GAO, Chuanjun; TAJAMMUL, Sabiha; MOHAMMAD, Rahim; BISWAJEET, Ganguli; WO2013/110643; (2013); A1;,
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Related Products of 72291-30-6,Some common heterocyclic compound, 72291-30-6, name is Methyl 2-cyano-2-methylpropanoate, molecular formula is C6H9NO2, 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.

The reactant and the catalyst are initially charged in the autoclave and the contents are inertized by purging with nitrogen. Subsequently, 5 bar of hydrogen are injected. The desired amount of ammonia is metered in and then the autoclave is heated slowly with stirring to the reaction temperature (80 C.). This step takes an average of 90 min, i.e. the delay time of the reactant solution in contact with ammonia is approx. 90 min. On attainment of the reaction temperature, hydrogen is injected rapidly to the pressure specified in Table 1 below and consumed hydrogen is replaced by metering under pressure control over the experiment time until no further hydrogen absorption is recorded.The autoclave experiments are carried out in a 2.5 l autoclave with hollow-shaft disk stirrer (stirrer speed approx. 600 rpm), electrical heating and jacket air cooling, 2 baffles, sparging through the autoclave lid and introduction of the hydrogen via the hollow-shaft stirrer. The weights for Raney catalysts are corrected for 10% water moisture, i.e., in real terms, 10% more water-moist catalyst is weighed out than specified. Reaction effluents are analyzed via gas chromatography (GC) (conditions: 60 m DB1701; internal diameter 0.32 mm; film thickness 0.25 mum; detector: FID; temperature program: 80 C.?10 K/min?280 C., 40 min, split ratio 100:1, carrier gas helium) and the compositions are reported in % by weight.The reactor yield is determined by means of gas chromatography with internal standard (I.S.) (I.S. piperidine; the concentration thus obtained in the crude effluent is multiplied by the total mass of the crude effluent and the yield thus calculated is compared to the theoretical yield). The reactions are all carried out with methyl 2-cyano-2,2-dimethylacetate with a purity of >99.8%. The main product obtained is aminopivalinamide (3-amino-2,2-dimethylpropionamide). TABLE 1 Pressure/ % by weight ConcentrationNH3/ Purity Conversion Reactor Example bar Catalyst of catalyst Solvent % nitrile (crude, GC) % % yield % 1 200 Ra-Ni 10 NMP 30 20:1 98.7 100 not determined 2 65 Ra-Co 10 BuOH 40 7.7:1 98.8 100 94.0% 3 65 Ra-Ni 10 BuOH 40 7.7:1 98.2 99.7 90.6% 4 65 Ra-Ni 2.5 BuOH 40 3:1 93.7 99.7 84.9% 5 65 Ra0Co 2.5 BuOH 40 3:1 94.9 99.9 86.7 6 65 Ra-Co 5 MeOH 40 3:1 96.5 99.1 90.4 7 65 Ra-Co 5 MeOH 40 3:1 96.6 99.1 91.1 8 65 Ra-Co 5 BuOH 40 3:1 90.0 99.4 88.2 The examples show that very good selectivities of at least 90% are achievable with Raney nickel and Raney cobalt. The higher the amount of ammonia, the higher the catalyst concentration and the higher the hydrogen pressure, the better is the selectivity. In example 8, a metal determination is carried out, 430 ppm of Co are found in the reaction effluent.

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

Reference:
Patent; BASF SE; US2008/306299; (2008); 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. 519059-09-7, name is 5-(Cyanomethyl)-2-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C9H5FN2

Step 1: 5-[(6-Chloro-5-isopropylpyridazin-3-yl)(cyano)methyl]-2-fluorobenzonitrile (G1) To an ice-cold solution of 5-(cyanomethyl)-2-fluorobenzonitrile (1 eq) and 3,6-dichloro-4-isopropylpyridazine (1.3 eq) (Reference: Org. Prep.+Proc. Int. 1988, 20, 117 and U.S. Pat. No. 4,628,088, 1986) in THF (38 mL, 0.1 M) was added portionwise NaH (1 eq). The reaction was stirred at 0 C. for 15 min and then warmed to RT and stirred for 2 hrs. The reaction was quenched with a sat. aq. NaHCO3 and extracted with EtOAc. The combined organic fractions were washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The crude was purified by silica gel chromatography, eluding with petroleum ether:EtOAc (8:2) to afford the title compound. 1H NMR (400 MHz, CDCl3) delta: 7.80-7.79 (2H, m), 7.49 (1H, s), 7.31-7.29 (1H, m), 5.63 (1H, s), 3.34-3.28 (1H, m), 1.36-1.29 (6H, m). MS (ES) C16H12ClFN4 required: 314/316, found: 315/317 (M+H)+.

The synthetic route of 519059-09-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jones, Philip; Kinzel, Olaf; Pescatore, Giovanna; Llauger Bufi, Laura; Schultz-Fademrecht, Carsten; Ferrigno, Federica; US2009/176765; (2009); A1;,
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Reference of 77326-36-4, 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. 77326-36-4, name is 2-Amino-6-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Sodium hydride 60% w/w in oil (87 mg, 2.28 mmol)was added portionwise to N-Boc-piperidine-2-methanol(0.49 g, 2.28 mmol) in THF (7.6 mL) at 0 oC over a period of 10 min.The resulting solution was stirred at 0 oC for 1 hr. Then 2-amino-6-fluorobenzonitrile(0.28 g, 2.05 mmol) was added in one-portion and the mixture heatedat 85 oC for 2 h. The reaction mixture was quenched with water (2mL) and then evaporated. The residue was diluted with ethyl acetate (30 mL) andwashed with a saturated aqueous solution of sodium bicarbonate (2 x 30 mL). Theorganic layer was dried over sodium sulphate, filtered and the solvent removed in vacuo. The residue was passed throughan SCX-2 ion exchange column (10 g) and the crude product eluted with 2Mammonia in methanol. Purification by flash column chromatography [SiO2,MeOH:DCM, 0-15%] afforded the corresponding product as a white powder (87 mg,0.38 mmol, 17%). Mp 102-103 oC; numax/cm-13311, 2925, 2211, 1577, 1476 and 1456; 1H NMR (500 MHz, CDCl3)delta = 7.18 (dd, J = 8.5 Hz, 1H), 6.30 (dd, J = 8.5, 1.0 Hz, 1H),6.20 (dd, J = 8.5, 1.0 Hz, 1H), 4.48 (s, 2H), 3.96 (dd, J = 9.0,3.7 Hz, 1H), 3.86 (dd, J = 9.0, 8.0 Hz, 1H), 3.14 (ddt, J = 11.5,4.0, 2.0 Hz, 1H), 3.10 – 2.97 (m, 1H), 2.78 (s, 1H), 2.71 (td, J = 11.9,2.7 Hz, 1H), 1.96 – 1.78 (m, 1H), 1.76 – 1.62 (m, 2H), 1.58 – 1.26 (m, 3H); 13CNMR (126 MHz, CDCl3) delta = 161.0, 151.1, 134.5, 115.4, 107.6, 100.4,86.7, 73.0, 55.4, 46.4, 28.3, 25.9, 24.1; LC-MS (TOF, 2.0 min) Rt= 0.59 min; m/z (ESI) 232 (M+H); Hi-Res LC-MS (ESI) m/z calcd for C13H18N3O (M+H) 232.1450, found 232.1452

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-Amino-6-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hensbergen, Albertus Wijnand; Mills, Vanessa R.; Collins, Ian; Jones, Alan M.; Tetrahedron Letters; vol. 56; 46; (2015); p. 6478 – 6483;,
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Electric Literature of 67832-11-5, 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. 67832-11-5, name is 4-Bromo-2-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Asolution of nBuLi in THF (2.5 M, 4.49 mL, 11.2 mmol) was added dropwise to astirred solution of 4-bromo-2-methylbenzonitrile (2.0 g,10.2 mmol) in dry THF (100 mL) at -78 C. and the solution stirred at -78 C.for 1 h. A stream of dry CO2 was bubbled through the solution for 10 min andthe mixture warmed to 20 C. The mixture was diluted with water (100 ml) andwashed with Et2O (3¡Á20 mL). The aqueous phase was acidified to pH 2 with cHCland extracted with CHCl3 (3¡Á50 mL) and the organic fraction was dried and thesolvent evaporated to give crude acid 171 (1.05 g, 64%)

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

Reference:
Patent; THEBOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY; AUCKLANDUNISERVICES LIMITED; SUTPHIN, PATRICK; CHAN, DENISE; TURCOTTE, SANDRA; DENNY, WILLIAMALEXANDER; HAY, MICHAELPATRICK; GIDDENS, ANNACLAIRE; BONNET, MURIEL; GIACCIA, AMATO; (181 pag.)JP5789603; (2015); B2;,
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Reference of 1735-88-2, 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. 1735-88-2 name is 2-Cyano-N-(4-fluorophenyl)acetamide, 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.

To a solution of 2-cyano-N-(4-fluorophenyl)acetamide (1.78 g, 0.01 mol) in ethanol (20ml) was added piperidine and 3,4-dihydroxy-5-nitrobenzaldehyde (1.83 g, 0.01 mol). The reaction mass was heated to 70-75 C for 2-3 hours. After completion of the reaction, the solid that formed was filtered off. To the solid was added demineralized water and the mixture was neutralized using diluted HCl. The residue was filtered off to afford the pure compound, which had a melting point of 250.3 – 253.9 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Cyano-N-(4-fluorophenyl)acetamide, and friends who are interested can also refer to it.

Reference:
Patent; GEORGETOWN UNIVERSITY; ALKEM LABORATORIES LIMITED; PADMANABHAN, Radhakrishnan; NAGARAJAN, Kuppuswamy; RAO, Kothapalli Sundarraja; SHRIDHARA, Kanakamajalu; SHASHIPRABHA, .; HARISHA, Attimogae Shivamurthy; WO2014/164667; (2014); A1;,
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Synthetic Route of 64248-64-2, These common heterocyclic compound, 64248-64-2, name is 2,5-Difluorobenzonitrile, 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: A mixture of benzonitrile 1 (10.0 mmol) and methylhydrazine (2.8 mL, 50.0 mmol) in EtOH (10.0 mL) was heated to reflux overnight. The mixture was cooled to rt and then concentrated. H2O (10.0 mL) and EtOAc (20.0 mL) were added to the residue. The organic layer was washed with H2O (10.0 mL), brine (10.0 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was subjected to silica-gel chromatography by using EtOAc/hexanes (1:1) as eluent to give the product 2.

Statistics shows that 2,5-Difluorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 64248-64-2.

Reference:
Article; Liu, Han-Jun; Hung, Shiang-Fu; Chen, Chuan-Lin; Lin, Mei-Huey; Tetrahedron; vol. 69; 19; (2013); p. 3907 – 3912;,
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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. 40497-11-8, name is Ethyl 2,3-dicyanopropanoate, A new synthetic method of this compound is introduced below., Recommanded Product: Ethyl 2,3-dicyanopropanoate

Example 11Preparation of 5-aminopyrazole (VII):; To 2,6-dichloro-4-trifluoromethyl aniline 230 g and acetic acid 150 ml was added 1.1m of nitrosyl sulphuric acid over one hour at 30C and maintained at 30C for one more hour. Heat the mass to 50-55C over ? hour and the absence of 2,6-dichloro-4-trifluoromethyl aniline was monitored. Cool the mass to 30C, and the excess nitrosyl sulphuric acid was destroyed.The above diazotized mass was added to a mixture of 250 ml of acetic acid, 162 g ethyl-2,3-dicyanoproprionate and 425 ml water over 4-5 hours maintaining temperature 0-5C. Further maintained at 0C / 2 hours, 5C / 1 hour, 10C / lhour, 15C / 1 hour. 800 ml water was added at 15C over ? hour, extracted the solution with 3×250 ml methylene dichloride. Layers were separated. Dichloromethane layer was washed with 250 ml water, cooled the dichloromethane layer to 0C and washed with 250 ml 8N aq. NH3 under stirring for one hour. Layers were separated, dichloromethane layer was taken and NH3 gas was passed at 0-5 C till free NH3 was observed on top of the condenser and maintained the reaction mass for 3-4 hours at 0-5C. Then 250 ml water was added, stirred for ? hour, layers were separated, extracted aq. layer with 2×100 ml dichloromethane, dichloromethane layer was dried with MgS04, dichloromethane layer was concentrated to dryness, to obtain 288 g of 5-amino-3-cyano-l-(2,6- dichloro-4-triflouromethyl phenyl)-pyrazole of 98% purity.

The synthetic route of 40497-11-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GHARDA, Keki Hormusji; WO2011/107998; (2011); A1;,
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