Category: nitriles-buliding-blocks

501-00-8, name is 2-(3-Fluorophenyl)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. COA of Formula: C8H6FN

Step 1: Methyl 4-cyano-4-(3-fluorophenyl)-3-(4-fluorophenyl)butanoate [0747] Under protective gas (Ar), 0.767 g (5.0 mmol) of (3-fluorophenyl)acetonitrile and 0.1 ml of sodium methoxide solution (30% in methanol) were added to 0.820 g (4.55 mmol) of methyl 3-(4-fluorophenyl)acrylate in 15.0 ml of toluene, and the mixture was stirred in a closed vessel at 65 C. for 15 h. The solvent was removed under reduced pressure, the residue was taken up in ethyl acetate and the mixture was washed twice with in each case 25 ml of water. The combined organic phases were dried over sodium sulphate and the solvent was removed under reduced pressure. Chromatography of the residue on silica gel (ethyl acetate/heptane=20:80) gave 0.950 g (57% of theory) of the diastereomeric methyl 4-cyano-4-(3-fluorophenyl)-3-(4-fluorophenyl)butanoate (erythro:threo=54:46 according to integration of the methyl singlets in the 1H-NMR in CDCl3 at 3.66 and 3.56 ppm).

The synthetic route of 501-00-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Mosrin, Marc; Jakobi, Harald; Angermann, Alfred; Gatzweiler, Elmar; Haeuser-Hahn, Isolde; Heinemann, Ines; Rosinger, Christopher Hugh; Lehr, Stefan; Schnatterer, Stefan; US2014/235446; (2014); A1;,
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Application of 403-54-3,Some common heterocyclic compound, 403-54-3, name is 3-Fluorobenzonitrile, molecular formula is C7H4FN, 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) 3-Cyano-4-nitrofluorobenzene m-Fluorobenzonitrile (96.8 g., 0.8 mole) is added in two and one-half hours to a mixture of concentrated sulfuric acid (600 ml.) and potassium nitrate (80.9 g., 0.8 mole) at 3-6 C., then allowed to warm to 25 C. The mixture is poured over cracked ice (3000 ml.), extracted with chloroform (5*250 ml.), dried and the solvent removed. The residue is extracted with pentane and dried to give 3-cyano-4-nitrofluorobenzene (115 g., 86.5%) m.p. 102-104 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Fluorobenzonitrile, its application will become more common.

Reference:
Patent; Rohm and Haas Company; US4358308; (1982); A;; ; Patent; Rohm and Haas Company; US4419122; (1983); A;; ; Patent; Rohm and Haas Company; US4419123; (1983); A;; ; Patent; Rohm and Haas Company; US4419124; (1983); A;,
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Adding a certain compound to certain chemical reactions, such as: 89001-53-6, name is 2-Methyl-4-nitrobenzonitrile, 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 89001-53-6, Quality Control of 2-Methyl-4-nitrobenzonitrile

To a refluxing mixture of 2-methyl-4-nitro-benzonitrile (32.4 g, 0.2 mol) and NBS (44.470 g, 0.25 mol) in CC14 (300 ml) was added AIBN (0.325 g) and the resultant reaction mixture was refluxed for 4 hours. The reaction mixture was treated with AIBN (0.325 g, 31 mmol) and refluxed further for 4 hours. The reaction mixture was filtered, and the filtered succinimide was washed with CCl4. The filtrate was concentrated in vacuo to provide a bromo compound (46 g). The bromo compound was dissolved in MeCN (200 ml), and to the reaction mixture was added homophthalic anhydride (30.780 g, 0.19 mol) at room temperature and under inert atmosphere. The reaction mixture was then treated with a solution of triethylamine (84 ml, 0.6 mol) in acetonitrile (100 ml). The reaction mixture was refluxed for 8 hours. The precipitate that formed was removed by filtration and washed with MeCN (100 ml). The washed precipitate was suspended in DMF (300 ml), which was heated at 130 C, then cooled and filtered. The resultant solid was washed with DMF (100 ml) and dried under vacuum to provide Compound 53a as a pale yellow solid (18.310 g, 33%). 1H-NMR (DMSO-d6): 8, 4.09 (s, 2H), 7.56 (m, 1H), 7. 81-7. 82 (m, 2H), 8.17 (d, J = 8.4 Hz, 1H), 8.26-8. 34 (m, 2H), 8.44 (s, 1H), 12.47 (s, 1H).

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Reference:
Patent; INOTEK PHARMACEUTICALS CORPORATION; WO2005/82368; (2005); A1;,
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Synthetic Route of 13531-48-1,Some common heterocyclic compound, 13531-48-1, name is Methyl 3-cyanobenzoate, molecular formula is C9H7NO2, 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: The reaction was carried out in a 100-mL stainless steel autoclave. Phenylcyanide (0.10 g, 1.00 mmol) was added to a mixture of ethylenediamine (0.12 g, 2.00 mmol), CoCl26H2O (0.24 g, 1.00 mmol) and Zn (0.07 g, 1.00 mmol) and the vessel was placed in an autoclave. For some of the reactions that were carried out in solvent, 5 mL of solvent was also added. The autoclave was pressurized to 5.00 atm with O2. The mixture was stirred in a preheated oil bath at 120 C for 12 h. Then, the reaction mixture was cooled to room temperature and the product was purified by column chromatography on silica gel using n-hexane:CH2Cl2 (1:1) to give the benzamide(88 % yield).

The synthetic route of 13531-48-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Keshipour, Sajjad; Shaabani, Ahmad; Research on Chemical Intermediates; vol. 41; 8; (2015); p. 5071 – 5078;,
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These common heterocyclic compound, 368-77-4, name is 3-(Trifluoromethyl)benzonitrile, 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: C8H4F3N

General procedure: Sodium azide, 11.4 mmol, and dimethylamine hydrochloride, 11.2 mmol, were dissolved in 10 mL of DMF, 10 mmol of the corresponding nitrile and 5 mL of DMF were added, and the resulting suspension was heated for 8 h at 110-115C. The mixture was cooled and filtered from the precipitate of sodium chloride, and the precipitate was washed with 10 mL of DMF on a filter. The filtrate was diluted with 30 mL of cold water and acidified with 10% aqueous HCl to pH 2-3. The precipitate was filtered off, thoroughly washed with cold water (3*30 mL), and dried in air. The physical constants and spectral parameters of 3a-3j were in agreement with published data [13, 14].

The synthetic route of 3-(Trifluoromethyl)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Seliverstova; Suslonov; Zarubaev; Trifonov; Russian Journal of Organic Chemistry; vol. 54; 4; (2018); p. 633 – 638; Zh. Org. Khim.; vol. 54; 4; (2018); p. 630 – 635,6;,
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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. 17983-30-1, name is 3-Oxocyclohexanecarbonitrile, A new synthetic method of this compound is introduced below., Safety of 3-Oxocyclohexanecarbonitrile

Under a nitrogen atmosphere, lithium aluminum hydride (92 mg, 2.44 mmol) was added to a solution of 1-cyanocyclohexan-3-one (100 mg, 0.812 mmol) in tetrahydrofuran (2 ml) at room temperature, and the resulting mixture was refluxed. After 5 hours, water, an aqueous sodium hydroxide solution and water were added in that order to the reaction solution, and the resulting mixture was filtered under reduced pressure. Thereafter, 1M-hydrochloric acid-diethyl ether (974 mul, 0.974 mmol) was added to the filtrate. The resulting mixture was concentrated under reduced pressure, and to an aqueous solution (4 ml) of the resulting residue were added potassium carbonate (202 mg, 1.46 mmol), ethoxycarbonylphthalimide (196 mg, 0.893 mmol) and acetonitrile (1 ml) at room temperature. After 21 hours, the reaction solution was poured into water and extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) and purified again by a silica gel column chromatography (eluent: chloroform/ethyl acetate) to obtain cis-2-[(3-hydroxycyclohexyl)methyl]-1Hisoindole-1,3(2H)-dione (83.5 mg, 40%, cis : trans = 12 : 1).

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; Sumitomo Pharmaceuticals Company, Limited; EP1403255; (2004); A1;,
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Electric Literature of 216976-30-6, The chemical industry reduces the impact on the environment during synthesis 216976-30-6, name is 3-Fluoro-5-methylbenzonitrile, I believe this compound will play a more active role in future production and life.

Step 1: 3-(Bromomethyl)-5-fluorobenzonitrile3-Fluoro-5-methylbenzonitrile (Hognda Trading; 100 g, 0.74 mol) was taken in acetonitrile (1 L) at 25C under nitrogen atmosphere. N-Bromosuccinimide (105 g, 0.59 mol) and AIBN (2.4 g, 0.014 mol) were added and the reaction mixture was heated at 70C for 1 h 20 minutes. The reaction mixture was cooled to 25C and concentrated. The residue was diluted, cooled to 0- 5C and stirred for 15 minutes at the same temperature. The precipitated succinimide was filtered and the filtrate was concentrated to get crude product as yellow oil (90 g). It was taken in petroleum ether (200 mL) and cooled to -20C stirred for 30 minutes. The precipitated solids were filtered and dried to get the title product as white solid. 1H NMR (DMSO-d6; 400 MHz): delta 7.83 (m, 2H), 7.73 (m, 1 H), 4.72 (s, 2H). HPLC (Method A) Rt: 4.17 min (Purity: 99.4%).

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, 3-Fluoro-5-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SERONO S.A.; BOMBRUN, Agnes; QUATTROPANI, Anna; GONZALEZ, Jerome; DORBAIS, Jerome; KNIGHT, Chris; BAKER-GLENN, Charles; WO2012/4287; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 40497-11-8, name is Ethyl 2,3-dicyanopropanoate, 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 40497-11-8, Application In Synthesis of Ethyl 2,3-dicyanopropanoate

In a 250 mL round bottom three-necked flask, 0.01 mol of 2-methylaniline and a small amount of ethanol were added,3.0 mL (0.035 mol) of concentrated hydrochloric acid was added dropwise under ice-cooling with stirring.0.018 mol of sodium nitrite was dissolved in 10 mL of water,Slowly drop into the flask, drop finishedAfter reaction 0.5h yellow diazonium salt solution.0.01 mol of ethyl 2,3-dicyanopropionate was added to a three-necked flask,The prepared diazonium salt solution was dropped into the flask,After dropping the reaction for 2 h.Adding ammonia,Adjust the pH to 9-10,Reaction at room temperature for 2h.After completion of the reaction, the reaction mixture was extracted with 40 mL of dichloromethane,The organic layer was washed with water (2 x 30 mL)Washed with saturated sodium chloride solution (1 x 40 mL)Dried over anhydrous magnesium sulfate,A portion of the solvent was evaporated under reduced pressure to crystallize 1.30 g of product,Yield 66.7%

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Nanjing University of Technology; Wan, Rong; Wu, Shaohua; Guo, Chunwei; Wang, Xinlin; Chen, Fuli; Han, Zhenyu; Fu, Xiaohuan; (13 pag.)CN105820167; (2016); A;,
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Electric Literature of 3672-47-7, A common heterocyclic compound, 3672-47-7, name is 3-(4-Methoxyphenyl)-3-oxopropanenitrile, molecular formula is C10H9NO2, 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: Fresh cells and lyophilised cells of Rhodotorula rubra MIM147 were used 20gL-1 dry weight re-suspended in phosphate buffer or in tap water with 50gL-1 of glucose; then the substrates 1, 3-10 were dissolved in DMSO and added at 2gL-1 concentration. For substrate 1, biotransformations were also carried out at 4, 6 or 10gL-1 concentration.

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; Rimoldi, Isabella; Facchetti, Giorgio; Nava, Donatella; Contente, Martina Letizia; Gandolfi, Raffella; Tetrahedron Asymmetry; vol. 27; 9-10; (2016); p. 389 – 396;,
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Reference of 10406-25-4,Some common heterocyclic compound, 10406-25-4, name is 4-(Aminomethyl)benzonitrile, molecular formula is C8H8N2, 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: Carborane-1-carboxylic acid (1.0 equiv) and COMU (1.1 equiv) dissolved in DMF, acetone or ethylacetate were reacted with the amine (1.2 equiv) and N,N-diisopropylethylamine (DIPEA, 2.0 equiv) dissolved in DMF, acetone or ethylacetate for 25minat room temperature and purified using the eluent ratio given below. Synthetic details of the optimized procedure in DMF and analytical data of compounds not listed below have recently been reported [33].

The synthetic route of 10406-25-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Scholz, Matthias S.; Wingen, Lukas M.; Brunst, Steffen; Wittmann, Sandra K.; Cardoso, Ian L.A.; Weizel, Lilia; Proschak, Ewgenij; European Journal of Medicinal Chemistry; vol. 185; (2020);,
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