Category: nitriles-buliding-blocks

Some common heterocyclic compound, 939-80-0, name is 4-Chloro-3-nitrobenzonitrile, molecular formula is C7H3ClN2O2, 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 4-Chloro-3-nitrobenzonitrile

General procedure: The respective N-alkoxysalicylamide 10 (2 mmol) and 1,2-dihaloarene (1-halo-2-nitroarene) partner 2 (2 mmol) were combined in anhydrous DMF (7 mL) with freshly calcinated K2CO3 (829 mg, 6 mmol) and the mixture was kept, with stirring, at the temperature and for the time period indicated in Table 2. DMF was removed in vacuo and the residue was treated with water (10 mL), which caused a viscous oil to separate. It was extracted with CH2Cl2 (5 mL), the organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel using an appropriate gradient of CH2Cl2 in hexanes as eluent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 939-80-0, its application will become more common.

Reference:
Article; Sapegin, Alexander; Reutskaya, Elena; Smirnov, Alexey; Korsakov, Mikhail; Krasavin, Mikhail; Tetrahedron Letters; vol. 57; 52; (2016); p. 5877 – 5880;,
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Some common heterocyclic compound, 4640-67-9, name is 3-(4-Fluorophenyl)-3-oxopropanenitrile, molecular formula is C9H6FNO, 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. name: 3-(4-Fluorophenyl)-3-oxopropanenitrile

General procedure: Under argon atmosphere, the corresponding beta-ketonitrile 2(1 mmol), water (3 mL), the ruthenium(II) complex 1 (0.028 g,0.05 mmol; 5 mol%) and NaO2CH (1.360 g, 20 mmol) were introducedinto a Teflon-capped sealed tube, and the reaction mixturestirred at 100 C for 24e48 h. The solvent was then removed undervacuum and the resulting solid residue purified by flash columnchromatography over silica gel using, unless otherwise stated, amixture of MeOH/EtOAc (1:10) as eluent. Characterization data forthe isolated beta-hydroxyamides are as follows:

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4640-67-9, its application will become more common.

Reference:
Article; Gonzalez-Fernandez, Rebeca; Crochet, Pascale; Cadierno, Victorio; Journal of Organometallic Chemistry; vol. 896; (2019); p. 90 – 101;,
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Application of 34916-10-4,Some common heterocyclic compound, 34916-10-4, name is 4-Oxo-cyclohexanecarbonitrile, molecular formula is C7H9NO, 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 3: LiHMDS (9.5 mL, 9.5 mmol) was added dropwise into a solution of compound 116-3 (1 g, 8 mmol) in THF (20 mL) at 0 C. After the addition, the reaction mixture was stirred for further 30min. Then PhN(SO2CF3) (3.6 g, 8.6 mmol) was added into the solution. The obtained mixture was stirred at 25C for 6h, finally quenched with H2O and extracted with EtOAc. The combined extraction liquid was washed with brines, dried over sodium sulfate and concentrated to dry to deliver sulfonate as yellow oil. The obtained sulfonate, Pd(dppf)Cl2 (80.4 mg, 0.11 mmol), bis(pinacolato)diboron (0.67 g, 2.6 mmol) and KOAc (0.65 g, 6.6 mmol) were added into dioxane (15 mL), under nitrogen gas atmosphere, the reaction mixture was heated to 100C and stirred for 18h. The reaction mixture was poured into H2O, extracted with EtOAc. The combined extraction liquid was washed with brines, dried over sodium sulfate and concentrated to dry, finally purified by column chromatography (PE:EtOAc = 5:1) to deliver compound 116-4 (0.5 g, yield 28%) as white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Oxo-cyclohexanecarbonitrile, its application will become more common.

Reference:
Patent; GUANGDONG ZHONGSHENG PHARMACEUTICAL CO., LTD; WU, Hao; LIN, Jun; LI, Yunhui; WEI, Changqing; CHEN, Shuhui; LONG, Chaofeng; CHEN, Xiaoxin; LIU, Zhuowei; CHEN, Lijuan; (212 pag.)EP3124482; (2017); A1;,
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Related Products of 658-99-1,Some common heterocyclic compound, 658-99-1, name is 2-(3,4-Difluorophenyl)acetonitrile, molecular formula is C8H5F2N, 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.

22.1.1 Synthesis of 3-cyano-3-(3,4-difluorophenyl)pentanedioic Acid Diethyl Ester Prepare by the method of Example 3.1.2 using 3,4-difluorophenylacetonitrile to give the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(3,4-Difluorophenyl)acetonitrile, its application will become more common.

Reference:
Patent; Maynard, George D.; Le, Tieu-Binh; US2001/34343; (2001); A1;,
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Some common heterocyclic compound, 868-54-2, name is 2-Aminoprop-1-ene-1,1,3-tricarbonitrile, molecular formula is C6H4N4, 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. HPLC of Formula: C6H4N4

General procedure: A solution of 0.264 g (2 mmol) of2-aminoprop-1-ene-1,1,3-tricarbonitrile and 0.088 g(2 mmol) of freshly distilled acetaldehyde in 5 mL of1,4-dioxane containing a catalytic amount of piperidiniumacetate was stirred for 2 h at 60C. A solution of0.320 g (2 mmol) of bromine in a mixture of 1 mL ofconcentrated aqueous HBr and 2 mL of 1,4-dioxanewas then added, and the mixture was stirred for 4 hat 70C. When the reaction was complete (TLC), themixture was cooled, neutralized to pH 7 witha 5% aqueous solution of sodium carbonate, anddiluted with 20 mL of water. A tarry material separatedand was ground in water until a solid precipitate wasobtained. It was filtered off, washed with a smallamount of isopropyl alcohol and distilled water, and recrystallized from ethyl acetate.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 868-54-2, its application will become more common.

Reference:
Article; Bardasov; Alekseeva, A. Yu.; Ershov; Russian Journal of Organic Chemistry; vol. 54; 7; (2018); p. 1106 – 1108; Zh. Org. Khim.; vol. 54; 7; (2018); p. 1098 – 1099,2;,
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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. 56043-01-7, name is 2-Amino-6-methylbenzonitrile, A new synthetic method of this compound is introduced below., Product Details of 56043-01-7

General procedure: 1mmol 2-aminobenzonitrile (118mg), 1.2mmol bromobenzene, 6.7mg Pd(OAc)2 (3mol%), 21.5mg CataCXium A (6mol%), 1.5mmol DBU (225mul), 0.5mmol Mo(CO)6 (132mg), and 4mL DMF were given in an argon flushed pressure tube, which was subsequently sealed. The mixture was heated to 130C under stirring for 16h. After cooling to room temperature, the crude mixture was diluted in ethyl acetate and washed with water. The aqueous phase was extracted twice with ethyl acetate. The organic layers were combined, dried over Na2SO4, and the solvent was removed under reduced pressure. Column chromatography (hexane/ethyl acetate 8:2) gave 176mg (79%) N-(2-cyanophenyl)benzamide (a1)

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; Wu, Xiao-Feng; Oschatz, Stefan; Sharif, Muhammad; Beller, Matthias; Langer, Peter; Tetrahedron; vol. 70; 1; (2014); p. 23 – 29;,
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These common heterocyclic compound, 154607-01-9, name is 4-Bromo-2-chlorobenzonitrile, 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: C7H3BrClN

Preparation of Intermediate 4-Bromo-2-chloro-benzaldehvde (l-3a):The 4-Bromo-2-chloro-benzaldehyde was prepared using procedures described in J. Med. Chem. 1981, 24, 1155-1161.4-bromo-2-chloro-benzonitrile (7.05g, 32.5 mmol) was dissolved in toluene (60 mL) and dichloromethane (1OmL) and cooled to -600C as a 1.5M solution of diisobutylaluminum hydride in toluene (33.4 ml, 49.8 mmol) was added dropwise over 30 minutes keeping the temperature between -60 and – 500C. The reaction was allowed to warm slowly to room temperature and stirred for an additional 3 hours. The reaction was quenched using ethyl acetate and stirred for 20 minutes before the addition of 1 N hydrochloric acid at O0C. The reaction was then allowed to warm slowly to room temperature. The reaction was extracted using ethyl acetate (2 times). Removal of the solvent provided the title compound (l-3a). 1H NMR (CDCI3): delta 7.52 (dd, 1H), 7.64 (d, 1H), 7.77 (d, 1H), 10.4 (s, 1 H)

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

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/59335; (2008); A1;,
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Related Products of 499983-13-0, 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 499983-13-0 as follows.

Ethylene carbonate (370.2 g, 4.204 mol, 30.0 eq.) was loaded in a 500 ml reactor at room temperature and heated to an internal temperature of 40C till all the solid melted. Then 1.4 g of PEG-200 (0.007 mol, 0.05 eq.) and 30.0 g of 4-bromo-3-fluorophenylacetonitrile (0.140 mol, 1.0 eq.) were charged in the reactor. Potassium tert-butoxide (31.4 g, 0.280 mol, 2.0 eq.) was added portion-wise, under stirring, to the resulting clear colorless solution. The internal temperature rose up to 60C. Then, the mixture was heated to 130C and kept under stirring for 8 hours. The mixture was cooled to 40C and then 105 g of toluene and 240 g of deionised water were added. The mixture was kept under stirring for 15 minutes at 40C and then stirring was stopped. After 15 minutes two layers were separated: a lower organic clear red phase and an upper aqueous colorless phase. The organic solution was reloaded into the reactor and heated to an internal temperature of 40C. 240 g of deionised water were added. The mixture was kept under stirring for 15 minutes at 40C and then stirring was stopped. After 30 minutes the yellowish opalescent aqueous layer (lower) was discarded and the organic phase was washed again two times with 240 g of deionised water. After 30 minutes, the yellowish opalescent aqueous layer was discarded. The organic solution was warmed to 80C and the volatile solvents were removed under reduced pressure until 36 ml as the final volume. A solution 9.6 g of isopropyl alcohol was added. The solution was cooled from 80C to 50C in 30 minutes and a small amount of seed was added. The crystallization mixture was cooled from 50C to 0C in 60 minutes. The suspension was stirred for at least 60 minutes then filtered washing three times with 9.0 g of a toluene/isopropyl alcohol mixture (1/1.25 w/w). The wet product was dried under vacuum at 40C for 15-18 hours. 22.7 g of a pale yellow solid were obtained (purity = 99,94%; molar yield = 68%).

According to the analysis of related databases, 499983-13-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ZaCh System S.p.A.; Verzini, Massimo; Cotarca, Livius; Guidi, Alberto; Melloni, Alfonso; Maragni, Paolo; EP2818460; (2014); 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. 52798-01-3, name is Methyl (4-cyanophenyl)acetate, A new synthetic method of this compound is introduced below., Product Details of 52798-01-3

Step S2:Compound 2 (212 g) was added to the reactor under nitrogen, and THF (3 L) and PMHS (269 g) were added and cooled to 0 C;NaBEt3H (120.7 g) was added dropwise with stirring at 0 to 10 C, warmed to room temperature and stirred for 20 hours (the product of this stage was analyzed by IPC).Cool to 0 ~ 10 C, slowly add 500 ml of methanol at 0 C, add 2 L of saturated NaCl aqueous solution,Stir for 15 minutes, separate, and the aqueous phase was extracted with 1L ethyl acetate.The combined organic layers were dried over Na2SO4, concentrated, and then applied107 g of Compound 3 (IPC retention time: 1.61 min) was obtained as a yellow solid.

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; Huidingzhiyao (Beijing) Technology Co., Ltd.; Wang Zaiqi; Yang Lihu; (20 pag.)CN108864114; (2018); A;,
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Reference of 60702-69-4, 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. 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Anhydrous p-toluene sulfonic acid (41.99 g, 220.76 mmol) was melted at 120 C and 3-amino-4-methoxy benzoic acid methyl ester (20 g, 110.38 mmol) obtained in step 1 of Preparation Example 1 and 2-chloro-4- fluorobenzonitrile (25.76 g, 165.57 mol) were added thereto and stirred at 160 C for 8 hours. The resulting solution was cooled to room temperature and the reaction was stopped by adding NaHCO3 thereto. The resulting mixture was extracted with ethyl acetate, the extract was dried over MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (26.70 g, 79.47 mmol) in a yield of 72 %. 1H NMR (CDCl3): delta 7.92-7.75 (4H, m), 7.15-7.02 (3H, m), 3.87-3.81 (6H, d) MW: 336

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-4-fluorobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CRYSTALGENOMICS, INC.; YUYU INC.; WO2004/65370; (2004); A1;,
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