Author: Jessica.F

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,
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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. 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,
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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

Related Products of 17354-04-0, 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. 17354-04-0, name is 2-(4,5-Dimethoxy-2-nitrophenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Piperidine (0.03 ml, 5 mol %) was added to a warm solution of the appropriate salicylaldehyde 5 (5 mmol) and 2-(4,5-dimethoxy-2-nitrophenyl)acetonitrile (1.12 g, 5 mmol) in EtOH (10 ml). The resulting solution was refluxed with stirring for 5 h. The mixture was treated with a solution of concentrated H2SO4 (0.55 ml) in EtOH (2 ml) and refluxed with stirring for 2 h. The obtained precipitate was filtered, washed with EtOH (10 ml), hot H2O (40 ml) and finally with EtOH (10 ml), and dried at 100 C.

The chemical industry reduces the impact on the environment during synthesis 2-(4,5-Dimethoxy-2-nitrophenyl)acetonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Article; Irgashev, Roman A.; Karmatsky, Arseny A.; Slepukhin, Pavel A.; Rusinov, Gennady L.; Charushin, Valery N.; Tetrahedron Letters; vol. 54; 42; (2013); p. 5734 – 5738;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 2141-62-0, name is 3-Ethoxypropanenitrile, 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 2141-62-0, Computed Properties of C5H9NO

EXAMPLE 1 2-(3-Amino-2-pyrazolin-1-yl)pyridine A 0.58 g. amount of sodium metal is dissolved in 150 ml. of absolute ethanol, then 14.0 g. of 2-hydrazinopyridine is added followed by 12.7 g. of betaethoxypropionitrile. The reaction mixture is refluxed on a steam bath for 16 hours, then the solvent is removed in vacuo. Water is added and the solid collected by filtration. The solid is recrystallized twice from acetone to give 5.55 g. of the product of the Example as tan colored crystals, m.p. 168.5-171 C.

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

Reference:
Patent; American Cyanamid Company; US4622401; (1986); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 53005-44-0,Some common heterocyclic compound, 53005-44-0, name is 2-Methoxy-6-methylbenzonitrile, molecular formula is C9H9NO, 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 a solution of 2-bromo-3-methylphenol (10.0 g, 53.5 mmol) in DMF (60 ml) was added sodium hydride (2.78 g, 69.5 mmol) in small portions at 0 C, which was followed by addition of Mel (6.69 mL, 107 mmol). TLC showed formation of a slightly less polar spot right away. The reaction was diluted with EtOAc (400 mL), washed with water 3 times, dried over Na2S04, and concentrated. The crude product was used in the next step without further purification. To the flask charged with the above material and a stir bar was added CuCN (9.9 g, 109 mmol) and DMF (100 mL). The mixture was purged three times with nitrogen, and heated to 150 C for 24 hours. TLC showed formation of a more polar spot. . The reaction was cooled to RT, diluted with DCM (400 mL), and filtered through a pad of celite to remove the solids. The filtrate was washed with saturated NH4Oac and brine, dried over sodium sulfate, concentrated to afford a brownish solid (4.8g, 60% yield). The resulting nitrile was used in the following step without further purification. To a flask charged with the nitrile and a stir bar was added NBS (6.4 g, 36 mmol) and TFA (60 mL). The reaction was allowed to stir at RT for 16 hours. TLC showed clean formation of a slightly more polar spot. The solvent was removed under vacuum, and the residue was purified by silica gel flash chromatography. After removal of solvent, 3-bromo-6-methoxy-2-methylbenzonitrile was collected.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Methoxy-6-methylbenzonitrile, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PIO, Barbara; PASTERNAK, Alexander; SHAHRIPOUR, Aurash; TANG, Haifeng; WALSH, Shawn; WO2013/90271; (2013); A1;,
Nitrile – Wikipedia,
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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 66389-80-8 as follows. SDS of cas: 66389-80-8

To a round-bottom flask equipped with a stir bar was added 18a-b (1.0 eq), hydroxylamine hydrochloride (2.0 eq), NaHCO3 (4.0 eq), and methanol (10mL/mmol). The reaction was refluxed and stirred in a pre-heated 75C oil-bath for 6h. After cooling to room temperature, the precipitate was filtered off and washed with methanol. The filtrate was concentrated in vacuo and further purified on a silica gel column. 4.2.4.5 tert-Butyl (E)-(4-(N?-hydroxycarbamimidoyl)benzyl)carbamate (19a) Yield: 65%. MP: 142-145C. 1H NMR (400MHz, DMSO-d6) delta 9.57 (s, 1H, -OH), 7.61 (d, J=8.1Hz, 2H, -ArH), 7.40 (t, J=6.1Hz, 1H, -NHCO-), 7.22 (d, J=8.1Hz, 2H, -ArH), 5.77 (s, 2H, -NH2), 4.13 (d, J=6.1Hz, 2H, -ArCH2-), 1.40 (s, 9H, -CH3)

According to the analysis of related databases, 66389-80-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Luo, Zonghua; Rosenberg, Adam J.; Liu, Hui; Han, Junbin; Tu, Zhude; European Journal of Medicinal Chemistry; vol. 150; (2018); p. 796 – 808;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 86770-80-1, name is 3,3-Difluorocyclobutanecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 86770-80-1

Zinc metal (0.558 g, 10 micron dust, 8.5 mmol) was stirred in THF (2.5 ml) and methane sulphonic acid (0.04 mmol) was added and refluxed at 76 C. for 10 minutes. To this was added 3,3-difluoro-cyclobutanecarbonitrile (500 mg, 4.3 mmol, prepared according to Elend et al. Synth Comm, 2005, 35, 657) and the reaction mixture was heated for a further 10 minutes. Ethyl bromoacetate (0.751 ml, 6.8 mmol) dissolved in THF (0.5 mL) was then injected over a 2 hour period with the aid of a syringe pump and after the addition the mixture was stirred for a further 30 minutes. Aqueous HCl (3 ml of 3 M solution) was added drop-wise at 0 C. and the reaction mixture was then stirred for 17 hours between 0 and 20 C. The reaction mixture was analyzed by MS and TLC which showed the formation of the product and the consumption of the starting material and the reaction was worked up with (2×20 ml) water and (2×20 ml) ethyl acetate, the organic portion was then dried (Na2SO4) and reduced in vacuo. The product was isolated and purified using flash chromatography (AcOEt 7:93 heptane) and 3-(3,3-difluoro-cyclobutyl)-3-oxo-propionic acid ethyl ester (599 mg, 68% yield) was obtained as a colourless liquid. MS (ESI+): 207.1 ([M+H]+).

According to the analysis of related databases, 86770-80-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Amrein, Kurt; Hunziker, Daniel; Kuhn, Bernd; Mayweg, Alexander V.; Neidhart, Werner; US2007/49574; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts