Month: February 2021

Application of 439117-38-1, 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 439117-38-1 as follows.

Step C. [2-(aminomethyl)-5-chlorophenyl]methanol To LAH (1 M/Et2O, 104.4 ml, 104.4 mmol) in anhydrous THF (300 ml) at0 C. was added methyl 5-chloro-2-cyanobenzoate (9.28 g, 0.512 mmol) maintaining the temperature below 20 C. After one half hour, quenched at 0 C. with water (3.97 ml), NaOH (1N, 11.9 ml, 11.9 mmol) and water (3.97 ml). A precipitate was filtered out and washed with THF. The filtrate was concentrated in vacuo and was used immediately in the next step. H NMR (CDCl3, 400 MHz): delta7.17-7.36 (m, 3 H); 4.60 (s, 2 H); 3.98 (s, 2 H);

According to the analysis of related databases, 439117-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Barrow, James C.; Coburn, Craig; Selnick, Harold G.; Ngo, Phung L.; US2002/193398; (2002); 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. 10406-25-4, name is 4-(Aminomethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 10406-25-4

General procedure: In a stainless reactor bomb, the corresponding aliphatic amine (1.0mmol), 1c (0.50 mol%), K2CO3 (5.0 mol%), and MeOH (1.0 mL) were placed. Then, the reactor was sealed with a stainless stopper, and the mixture was stirred under indicated conditions. After removing MeOH under reduced pressure, the products were isolated by silicagel column chromatography.

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 10406-25-4.

Reference:
Article; Toyooka, Genki; Tuji, Akiko; Fujita, Ken-Ichi; Synthesis; vol. 50; 23; (2018); p. 4617 – 4626;,
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Related Products of 38469-83-9, The chemical industry reduces the impact on the environment during synthesis 38469-83-9, name is 4-Methoxy-2-nitrobenzonitrile, I believe this compound will play a more active role in future production and life.

EXAMPLE 2 2-Amino-4-methoxybenzamide To a solution of 37.4 g (0.210 mol) of 4-cyano-3-nitroanisole in 500 mL of ethanol was added 221.6 g (0.982 mol) of tin(II) chloride dihydrate. The reaction mixture was stirred and heated under reflux for 1 hour. After cooling to room temperature, the reaction mixture was poured onto ice. Aqueous sodium bicarbonate was added slowly to the ice mixture until the solution reached pH 7-8. Additional water was added to the mixture, which was then extracted with methylene chloride (2*400 mL) and ethyl acetate (1*300 mL). The separated aqueous layers were filtered between each of the extractions. The off white residue collected on the filters was rinsed with methylene chloride and ethyl acetate several times. The combined organic phases were then dried over magnesium sulfate, filtered and evaporated in the rotary evaporator to obtain 28.5 g crude product (mp 154-155 C.). Elemental analysis for C8 H10 N2 O2: Calc’d: C, 57.82; H, 6.07; N, 16.86; Found: C, 57.95; H, 5.95; N, 16.78.

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-Methoxy-2-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; American Home Products Corporation; US5948775; (1999); A;,
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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. 61150-58-1, name is 2-(2-Bromo-4-fluorophenyl)acetonitrile, A new synthetic method of this compound is introduced below., Product Details of 61150-58-1

Add potassium hydroxide (8.39 g, 150 mmol) and tetrabutylamine bromide(0.3 g, catalytic) to a solution of 2-(2-bromo-4-fluorophenyl)acetonitrile (4 g, 18.69 mmol) and 1,3-dibromopropane (4.15 g, 20.5 mmol) in toluene (20 mL). Stir it at 100 0C temperature for 2 h. Dilute the mixture with water and extract with ethyl acetate. Wash the organic layer with 1 N HCl and aqueous saturated sodium chloride. Dry over magnesium sulfate. Remove the organic solvent to give the crude product.Distill to give l-(2-bromo-4-fluorophenyl)cyclobutanecarbonitrile (boiling point 110- 120 C/0.3 Torr.) (1.5 g, 31 %). MS (GC) m/z 253 [M]+.Add 6 mL of HCl saturated methanol to the above solid and stir overnight. Evaporate the solvent to dry. Add NaHCO3 (1 M, 30 mL) and ether (20 mL). Stir for 15 min. Separate the organic layer and extract the aqueous layer with ether. Combine the ether solution and remove the solvent. Dissolve the residue in methanol (10 mL) and KOH (1.5 g) and stir over the weekend. Remove methanol and add water (30 mL). Extract with ethyl acetate and then acidify the aqueous layer with HCl. Extract the acidic solution with ethyl acetate, dry over MgSO4, and remove the solvent to give the title compound (1.0 g, 24 %). MS (ES) m/z 271 [M-I]”.

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; ELI LILLY AND COMPANY; WO2008/144223; (2008); A2;,
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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. 102151-33-7, name is 3-Chloro-4-methoxybenzonitrile, A new synthetic method of this compound is introduced below., name: 3-Chloro-4-methoxybenzonitrile

To a solution of N,N-diethyl-4-methoxy-2-methylbenzamide (1 g, 4.52 mmol) in THF (9 ml) at -78 C. was added dropwise tert-butyllithium 1.7 M in pentane (3.19 ml, 5.42 mmol) and the solution was stirred for 0.5 h before addition of 3-chloro-4-methoxybenzonitrile (0.757 g, 4.52 mmol) in THF (9 ml). The resulting solution was warmed to rt and stirred for 16 h. The reaction mixture was quenched with water, neutralized with 1 N HCl. The precipitated solid was collected and washed with water to give 3-(3-chloro-4-methoxyphenyl)-6-methoxyisoquinolin-1-ol (1.2 g, 84% yield) as a solid after drying. MS: MS m/z 316.1 (M++1)

The synthetic route of 102151-33-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; Hiebert, Sheldon; Rajamani, Ramkumar; Sun, Li-Qiang; Mull, Eric; Gillis, Eric P.; Bowsher, Michael S.; Zhao, Qian; Meanwell, Nicholas A.; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Babu, P.V.K. Suresh; Scola, Paul Michael; (403 pag.)US9527885; (2016); B2;,
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Application of 2469-99-0, These common heterocyclic compound, 2469-99-0, name is 3-Oxobutanenitrile, 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: First of all, a mixture of 3-oxoalkanonitrile (1 mmol) and hydrazine hydrate (55% aq) (2 mmol) was magnetically stirred in ethanol (5 ml) for 2h under room temperature condition. After completion of the reactions, which was followed by TLC EtOAc:n-hexane 3:1, 2-phthaldehydic acid (1 mmol), CH-acid (1 mmol), and 4-toluenesulfonic acid (0.3mmol) as catalyst were added. Then, the mixture magnetically stirred for 22 h under reflux condition. Reaction solvent was removed by vacuum and participate was washed with methanol. Finally, the residue was purified by recrystallization in mixture of DMSO/methanol (5:2).

The synthetic route of 2469-99-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Alizadeh-Kouzehrash, Meysam; Rahmati, Abbas; Tetrahedron; vol. 76; 7; (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. 31643-49-9, name is 4-Nitrophthalonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 31643-49-9

The synthesis of 2 was similar to 1, but 4-hydroxybenzaldehyde wasemployed instead of dimethoxy phenyl ethanol. The reaction mixturewas stirred under N2 at room temperature for 24 h. The other reagentswere 4-nitrophthalonitrile (1 g, 5.55 mmol) and anhydrous K2CO3 (2 g,13.88 mmol). Compound 2 was obtained as: White solid; m.p. 350 C;yield 67%; FTIR (KBr) (n cm-1): 3077 (Ar-CH), 2227 (C?N), 1601(C=C), 1263 (C-O-C); 1H NMR (400 MHz, DMSO-d6): delta 7.49 (d,1H, H2¡é), 7.56 (d, 1H, H6¡é), 7.70 (d,1H, H3¡é), 7.74 (d, 1H, H5¡é), 7.86 (d,1H, H5), 7.89 (s, 1H, H3), 8.15 (d, 1H, H6), 10.02 (s, 1H, Hald); 13C NMR(100 MHz, DMSO-d6, tamb): delta 109.3 (C1), 115.7 (C2), 116.2 (C4¡é), 117.3(CN), 116.2 (CN), 120.8 (C2¡é), 123.6 (C6¡é), 126.7 (C3¡é,5¡é), 132.0 (C3),136.8 (C5), 138.8 (C6), 155.1 (C4), 160.8 (C1¡é), 192.7 (Cald); ESI-SMHRm/z: 249.23 [M + H]+. Anal. calcd for C15H8N2O2: C, 72.57; H, 3.24; N,11.28; found: C, 72.4; H, 3.1; N, 11.2%.

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; Medyouni; Hallouma; Mansour; Al-Quraishy; Hamdi; Journal of Chemical Research; vol. 41; 5; (2017); p. 291 – 295;,
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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. 1441723-24-5, name is 4-Amino-2-fluoro-5-methoxybenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Amino-2-fluoro-5-methoxybenzonitrile

General procedure: In a sealed vial, i-(benzenesulfonyl)-6-chloro-indole-3-sulfonyl chloride XII-19 (i92 mg, 0.49 mmol) was dissolved in pyridine (4 mL) under argon. 2,i,3-benzoxadiazol-5-amine(i35 mg, i mmol) was added and stirred at room temperature overnight. The reaction mixture was evaporated to dryness then the residue was taken into DCM. The organic phase was washed with HCI i N and brine, dried over Mg504 and evaporated. The dark oil residue solidified on standing and was then triturated in ACN/water (8/2), sonicated and filtered, washed with water and dried under vacuum to provide i70 mg of ii(benzenesulfonyl)-N-(2,i ,3-benzoxadiazol-5-yl)-6-chloro-indole-3-sulfonamide 1-201 a as a yellow solid.Yield: 7i%.Basic LCMS Method i (ES-): 487 (M-H)-, iOO % purity.1H NMR (400 MHz, DMSO-d6)oe ii.52(s, iH), 8.99(s, iH), 8.i6-8.iO (m, 2H), 7.98(d, J= i .8 Hz, i H), 7.9i (dd, J = 9.i, 3.2 Hz, 2H), 7.63 (t, J = 7.5 Hz, i H), 7.56 – 7.5i (m, 2H),7.43 – 7.36 (m, 2H), 7.25 (dd, J = 9.6, i .9 Hz, i H).

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; UCB PHARMA GMBH; MUELLER, Christa E.; PEGURIER, Cecile; DELIGNY, Michael Louis Robert; EL-TAYEB, Ali; HOCKEMEYER, Joerg; LEDECQ, Marie; MERCIER, Joel; PROVINS, Laurent; BOSHTA, Nader M.; BHATTARAI, Sanjay; NAMASIVAYAM, Vigneshwaran; FUNKE, Mario; SCHWACH, Lukas; GOLLOS, Sabrina; VON LAUFENBERG, Daniel; BARRE, Anais; (493 pag.)WO2018/122232; (2018); A1;,
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115279-57-7, name is 2-(4-Aminophenyl)-2-methylpropanenitrile, 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. COA of Formula: C10H12N2

Example 24; l-[4-(Cyano-dimethyl-methyl)-phenyl]- 3-{4-[2-(3-Hydroxy-propylamino)- pyrimidin-4-yloxy] -phenyl} -urea188 mg (1.16 mmol) lJ’-Carbonyl-diimidazol (CDI) were given to a solution of 175 mg (1.09 mmol) 4-(cyano-dimethyl-methyl)-phenylamine (Hicks, T.A., J. Med. Chem. 22 (1979) 1460-1464) in 4.0 ml dichloro-methane and stirred for 12 h.A solution of 284 mg (1.09 mmol) 3-[4-(4-Amino-phenoxy)-pyrimidin-2- ylamino]-propan-l-ol in 6 ml dichloromethane was added within 30 min. and the mixture stirred for 12 h at r.t. The reaction mixture was evaporated and the residue was purified by chromatography on silica gel (ethyl acetate). The obtained material was left overnight with dichloromethane, the precipitate filtered, washed with ether and dried. Yield: 180 mg (37%) of the title compound. MS: 447.58 (ESI+).eta-NMR(400Hz, [DJDMSO): delta = 1.59(br, 2H, CH2-CH2-CH2), 1.67(s, 6H, CH3), 3.22(br, 2H, CH2-NH), 3.38(br, 2H, CH2-OH), 4.37(br, IH, OH), 6.05(br, IH, 5- H-pyrimidine), 7.05(br, IH, CH2NH), 7.09(d, 2H, 3-H/5-H-Ar-NH), 7.41 (d, 2H,Ar-C-CN), 7.49(m, 4H, 2-H/6-H-Ar-NH, Ar-C-CN), 8.12(d, IH, 6-H-pyrimidine), 8.75(s, IH, urea-NH), 8.79(s, IH, urea-NH).

The synthetic route of 115279-57-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2008/77548; (2008); 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. 1223434-15-8, name is Methyl 4-bromo-2-cyanobenzoate, A new synthetic method of this compound is introduced below., name: Methyl 4-bromo-2-cyanobenzoate

Into a 100-mE 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed methyl 4-bromo-2-cyanobenzoate (2.0 g, 8.33 mmol, 1.00 equiv), ether (40 mE), 2-(propan-2-yloxy)propane propan-2-ol propan-2-yltitanium dihydrate (2.75 mE, 1.10 equiv). This was followed by the addition of EtMgl3r (3M) (5.5 mE, 2.00 equiv) dropwise with stirring at 0 C. The resulting solution was stirred for 3 hour at room temperature. The reaction was then quenched by the addition of 20 mE of hydrogen chloride (1M). The resulting solution was extracted with ethyl acetate (50 mEx2) and the organic layers combined and dried over anhydrous sodium sulfate. The residue was applied onto a silica gel colunm with ethyl acetate/petroleum ether (7/3). This resulted in 409mg (2 1%) of 6?-bromospiro[cyclopropane- 1,1 ?-isoindolin] -3-one as a yellow solid. EC-MS (ESj: mlz 238.00, 240.00 [MH], tR=0.79 mm, (1.90 minute run).

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; Arvinas, Inc.; Crew, Andrew P.; Berlin, Michael; Dong, Hanqing; Homberger, Keith R.; Qian, Yimin; Snyder, Lawrence B.; Wang, Jing; Zimmermann, Kurt; (504 pag.)US2018/215731; (2018); A1;,
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