Month: May 2021

Synthetic Route of 38791-62-7, The chemical industry reduces the impact on the environment during synthesis 38791-62-7, name is 4-Phenoxyphthalonitrile, I believe this compound will play a more active role in future production and life.

11.3 g of compound 1 was dissolved in 30 ml of methanol, added to 25 ml of 50% sodium hydroxide solution, heated to reflux for 48 h. After completion of the reaction, the pH was adjusted to about 3 with concentrated hydrochloric acid, precipitated by precipitation, filtered and dried to give 10.5 g of compound 2.

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

Reference:
Patent; BEIJING BETA PHARMA, INC.; (43 pag.)TWI582078; (2017); B;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 13519-90-9, A common heterocyclic compound, 13519-90-9, name is 4-Fluoroisophthalonitrile, molecular formula is C8H3FN2, 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.

To (1R,3S)-cyclohexane-1,3-diamine (1.0 g, 8.8 mmol) and 4-fluoroisophthalonitrile (2.7 g, 18.4 mmol)Triethylamine (5.4 ml) was added to a solution of 30 ml of dimethyl sulfoxide. The mixture was purged with nitrogen and heated to stir at 150 C for 3 hours. After cooling to room temperature, the reaction mixture was diluted with water (100 ml) and extracted three times with dichloromethane (100 ml). The organic extracts were combined and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography(230-600 mesh silica gel) purified,Elute with 0-80% ethyl acetate / hexane,Get the title compound,It was a white solid (2.6 g, 81% yield).

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; Sichuan Yi Lite Bio-pharmaceutical Co., Ltd.; Jiao Guansheng; Zhang Chengpan; (13 pag.)CN109160888; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 77532-78-6, The chemical industry reduces the impact on the environment during synthesis 77532-78-6, name is 2-Bromo-6-methylbenzonitrile, I believe this compound will play a more active role in future production and life.

A. N-Butyl-2,3-difluoro-N-[1-(2-piperidin-1-ylmethyl-benzyl)-1H-benzoimidazol-2-ylmethyl]-benzamide A solution of 35 g (0.18 mole) of cyanobromotoluene and 16.18 g (0.19 mole) of piperidine in 300 mL of anhydrous DMF was treated with 73 g (0.5 mole) of K2CO3 at 50 C. for 2 hr. The reaction mixture was filtered through a plug of Celite, washed with 400 mL of ethyl acetate, and the filtrate was partitioned between ethyl acetate and 1/2 saturated brine. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo, yielding 36 g (0.18 mole) 100% of 2-Piperidin-1-ylmethyl-benzonitrile. 1H NMR (300 MHz, CDCl3) 7.6 (m, 3H), 7.24 (m, 1H), 3.6 (s, 2H), 2.4 (m, 4H), 1.5 (m, 6H).

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-Bromo-6-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DeSimone, Robert W.; Peterson, John; Steenstra, Cheryl; Shen, Yiping; Gustavson, Linda; Bakthavatchalam, Rajagopal; Hutchison, Alan; US2003/216390; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 138642-47-4, name is 2-Bromo-5-methoxybenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromo-5-methoxybenzonitrile

2-Bromo-5-methoxybenzonitrile (1.32 g, 6.23 mmol), 2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (1.36 g, 6.23 mmol), bis(triphenylphosphine)palladiumdichloride (0.437 g, 0.623 mmol) and potassium phosphate monohydrate (4.30 g, 18.68 mmol) were added to toluene (30 mL) and water (3 mL). The reaction mixture was degassed with bubbled nitrogen gas for 30 minutes before being refluxed under nitrogen for 15 h. After cooling, the reaction mixture was filtered through Celite and the organic layer was extracted with ethyl acetate. After removal of the solvents, the crude material was triturated with 40 mL of DCM followed by 50 mL of hexanes to give 8- methoxyphenanthridin-6-amine (0.95g, 68%) as a light yellow solid. The product was confirmed by GC/MS and NMR.

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; UNIVERSAL DISPLAY CORPORATION; XIA, Chuanjin; YEAGER, Walter; LI, David Zenan; FIORDELISIO, James; MA, Bin; ELSHENAWY, Zeinab; LAYEK, Suman; BARRON, Edward; KOTTAS, Gregg; BROOKS, Jason; WO2012/116231; (2012); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

906673-45-8, name is 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile, 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 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile

30.2 g (0.1 mol) of 4-[(4-bromo-3-hydroxymethyl)phenoxy)]benzonitrile, 300 ml of dichloromethane, and 30.3 g of triethylamine (0.3 mol) were added to the reaction kettle. The reaction was cooled to 0-10 C, 12.96 g of trimethylchlorosilane was added dropwise, the temperature was controlled to not exceed 10 C, stirred at 25 C for 24 h, quenched with water, extracted with dichloromethane, washed with water and dried over anhydrous magnesium sulfate, filtered, and the solvent was recovered to give an oil (31.8 g) , yield 85%;

The synthetic route of 906673-45-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wuhan Polytechnic University; Zhao Ling; Yang Bo; (8 pag.)CN108659024; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 17354-04-0, 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. 17354-04-0 name is 2-(4,5-Dimethoxy-2-nitrophenyl)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.

Example 6 5,6-dimethoxy-3H-indol-2-amine A solution of 2-(4,5-dimethoxy-2-nitrophenyl)acetonitrile (0.22 g, 1 mmol) in ethanol (15 ml) was treated with tin chloride (0.50 g, 2.2 mmol) and heated to 70 C. for 72 hours. The reaction mixture was allowed to cool to room temperature, extracted with EtOAc and washed with 1N NaOH and water. The combined organic extracts were dried over MgSO4, filtered and concentrated. HPLC purification provided 5,6-dimethoxy-3H-indol-2-amine (12 mg, 6.2%). 1H NMR (400 MHz, DMSO) delta 11.82 (s, 1H), 9.80 (s, 1H), 9.54 (s, 1H), 7.11 (s, 1H), 6.82 (s, 1H), 4.10 (s, 2H), 3.77 (s, 3H), 3.73 (s, 3H). MS (APCI) m/z 193 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4,5-Dimethoxy-2-nitrophenyl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; AbbVie Inc.; Pliushchev, Marina A.; Chiang, Gary G.; Pappano, William N.; Michaelides, Michael R.; Sweis, Ramzi F.; US2015/274660; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 34662-24-3, name is 2-Chloro-3-nitrobenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C7H3ClN2O2

2-Amino-4-cyano-1-N-[1-(3,3-diphenylpropyl)-piperidin-4-yl]aniline A mixture of 4-amino-1-(3,3-diphenylpropyl)piperidine di-trifluoroacetate (Method I) (500 mg, 0.96 mmol), 2-chloro,3-nitrobenzonitrile (373 mg, 2.04 mmol) and potassium carbonate (700 mg, 5.05 mmol) in DMSO (4 ml) was heated at 90 C. After 15 h the mixture was poured onto water and extracted with EtOAc (2*30ml). The organics were combined, washed with brine, dried (MgSO4), concentrated and purified by Bond Elut chromatography to give 4-cyano-2-nitro-1-N-[1-(3,3-diphenylpropyl)-piperidin-4-yl]aniline as an oil (300 mg, 0.68 mmol), MS: 442.

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; Burrows, Jeremy; Cumming, John; Mcinally, Thomas; US2003/119869; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 3100-67-2, name is 1-Amino-2-naphthonitrile, A new synthetic method of this compound is introduced below., Quality Control of 1-Amino-2-naphthonitrile

A solution of 1-amino-2-naphthonitrile (1.00 g, 5.95 mmol) in anhydrous ether (20 mL) was dropwise added to a solution of 1M 3-methoxyphenylmagnesium bromide-tetrahydrofuran solution (17.8 mL, 17.8 mmol) for 10 minutes. The mixture was heated under reflux for one hour. The reaction mixture was poured into 2N hydrochloric acid (30 mL). After addition of methanol (5 mL), the mixture was stirred for 4 hours at room temperature. The mixture was neutralized by addition of potassium carbonate, and the neutralized ether was subjected to extraction with ether. The ether portion was washed with saturated brine and dried over anhydrous sodium sulfate. The dried mixture was placed under reduced pressure to distill the solvent off. The residue was purified by silica gel column chromatography (chloroform/hexane=4/1), to give the titled compound (1.54 g, yield 93%). 1H NMR (CDCl3, 400 MHz) delta: 3.85 (3H, s), 6.98 (1H, d, J=9Hz), 7.06 (1H, dd, J=2, 8Hz), 7.1-7.2 (2H, m), 7.37 (1H, t, J=8Hz), 7.4-7.6 (4H, m), 7.5-7.6 (1H, m), 7.74 (1H, d, J=8Hz), 7.97 (1H, d, J=8Hz).

The synthetic route of 3100-67-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nippon Chemiphar Co., Ltd.; EP2058304; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 906673-45-8,Some common heterocyclic compound, 906673-45-8, name is 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile, molecular formula is C14H10BrNO2, 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.

In a three-necked flask, Compound II (20 g) was added, tetrahydrofuran (600 mL), trimethyl borate (14 g) was cooled to -78C, and butyllithium (64 mL, 2.5 M concentration) was added dropwise.The reaction was completed for 30 minutes or more. After the reaction was completed, 1N hydrochloric acid (600 mL) was added to quench the reaction, stirred for 30 minutes or longer, and allowed to stand for stratification.The organic phase was concentrated to dryness under reduced pressure, methanol (200 mL) was added to the resulting oil, concentrated hydrochloric acid (5 mL), and the mixture was stirred overnight at room temperature. After completion of the reaction, the mixture was concentrated under reduced pressure to give about 17 g of the target compound I.

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

Reference:
Patent; Yaoyuan Pharmaceutical Chemical (Shanghai) Co., Ltd.; Wang Yuan; Liu Chuanjun; Tang Wensheng; He Xungui; (8 pag.)CN107759625; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 79603-02-4, A common heterocyclic compound, 79603-02-4, name is 2-Bromo-6-nitrobenzonitrile, molecular formula is C7H3BrN2O2, 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.

Intermediate 11: 2-Nitro-6-cyclopropylbenzonitrile; [0176] 2-Bromo-6-nitrobenzonitrile (0.56g), cyclopropyl boronic acid (0.63g), palladium (II) acetate (0.055g), tricyclohexylphosphine (0.135g) and potassium phosphate tribasic (2.36g) were dissolved in a mixture of toluene (15mL) and water (3mL). The mixture was heated at 100C under nitrogen for 18 hours. The mixture was cooled and then partitioned between water and DCM. The organic solution was separated, dried with magnesium sulfate, filtered and the solvent was removed under vacuum. The residue was purified by flash chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane. The fractions containing the desired product were combined and evaporated to give the title compound as a light yellow solid (0.5 lg).NMR (CDCI3) delta 8.05 (d, IH), 7.64 (t, IH), 7.27 (d, IH), 2.52-2.45 (m, IH), 1.33-1.26 (m, 2H), 0.91-0.85 (m, 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; ZAFGEN CORPORATION; DYKE, Hazel, Joan; PALLIN, Thomas, David; CRAMP, Susan, Mary; WO2012/103333; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts