Category: 939-80-0

Reference of 939-80-0,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.

The starting material was prepared as follows: Diethyl malonate (44.6ml, 293 mmol) was added dropwise over 1.5 hours to a suspension of sodium hydride (11.7 g of a 60% suspension in mineral oil, 293 mmol) in DMF under argon and the reaction mixture was stirred at ambient temperature for 30 minutes. The resulting solution was added dropwise over 1 hour to a solution of 2-chloro-5-cyano-1-nitrobenzene (24.3 g, 133 mmol) in DMF (75 ml) cooled with a dry ice/acetone bath. The temperature of the cooling bath was adjusted to prevent the freezing of the red reaction mixture. After the addition was completed, the reaction was left to rise to ambient temperature over 2 hours. The resulting red solution was poured slowly into a stirred mixture of ice (100 ml) and 1M hydrochloric acid (10 ml). The resulting yellow precipitate was collected by filtration, washed with water until the filtrate was at pH7.0 and then dried under vacuum to give diethyl (4-cyano-2-nitrophenyl)malonate (39.6 g, 97%).

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

Reference:
Patent; Zeneca Limited; US6265411; (2001); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 939-80-0, 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. 939-80-0 name is 4-Chloro-3-nitrobenzonitrile, 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 3a Preparation of 4-chloro-3-aminobenzonitrile A degassed solution of 40 mmol of 4-chloro-3-nitrobenzonitrile (starting material) and 40 ml of xylene are placed in an autoclave (volume: 200 ml).5.0 mmol of TPPTS (in the form of 9.2 g of an aqueous solution containing 0.546 mol of TPPTS/kg of solution) as phosphine and 2.4 g (60 mmol) of NaOH, 23.8 ml of H2 O and 1.0 mmol of PdCl2 are added. The pH isfrom 10.5 to 11.0. The autoclave is closed, evacuated and filled with nitrogen. The evacuationand filling with nitrogen is repeated twice, then the autoclave is filled with CO, evacuated and refilled with CO. The evacuation and filling with CO is repeated twice. The autoclave is subsequently pressurized with CO to a pressure of 120 bar and the mixture is heated to 100 C. while stirring. The reaction time is 20 hours. The mixture is subsequently cooled to room temperature, the autoclave is emptied and the organic phase is separated from the aqueous phase. The organic phase is filtered to remove traces of palladiumand evaporated under reduced pressure, with the desired product being purified, if desired by crystallization or chromatography.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Chloro-3-nitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Hoechst Aktiengesellschaft; US5744643; (1998); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 939-80-0 as follows. 939-80-0

In a reactor, compound 2 (917 mg, 2.0 mmol), compound 4 (274 mg, 3.0 mmol) and Cs2CO3 (325 mg, 1.0 mmol) were added to dry THF (20 mL). Then the reactor was sealed under nitrogen, and the mixture was kept at 30 C., stirred for 12 hours. After the reaction, the mixture was diluted with dichloromethane (10 mL) and then filtered. The resulting filtrate was washed twice with water (2¡Á10 mL), and aqueous phases were combined, then the combined aqueous phases were extracted twice with dichloromethane (2¡Á10 mL). The organic layers were combined, dried over Na2SO4, and concentrated to obtain compound XVII as a light yellow powder (1004 mg, yield 90.2%), HPLC purity: 99.2%.

According to the analysis of related databases, 939-80-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; XU, YONG; (10 pag.)US2016/257667; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 939-80-0 as follows. 939-80-0

[00283] 4-(2,5-Dichlorophenoxy)-3-nitrobenzonitrile 34. 2,5-Dichlorophenol (17.86 g,109.54 mmol) and 4-chloro-3-nitrobenzonitrile (10.00 g, 54.77 mmol) were combined with K2CO3 (37.85 g, 273.85 mmol) in THF (300 niL). The reaction mixture was refluxed for 48 hrs and then the solid was filtered over a bed of Celite. After rinsing the residue with copious amounts of DCM, the filtrate was concentrated to produce a yellow solid. The solid was triturated with minimal DCM and collected via vacuum filtration to yield compound 34 (13.84 g, 81.7% yield, 100.0% pure). 1H NMR (500 MHz, DMSO-4): delta 8.73 (s, IH), 8.12 (dd, J1 = 9 Hz, J2 = 2 Hz, IH), 7.73 (d, / = 9 Hz, IH), 7.65 (d, / = 2 Hz, IH), 7.48 (dd, J1 = 9 Hz, J2 = 2 Hz, IH), 7.21 (d, / = 9 Hz, IH).

According to the analysis of related databases, 939-80-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AXIKIN PHARMACEUTICALS, INC.; LY, Tai, Wei; TRAN, Marie Chantal, Siu-ying; BAAUM, Erik, Dean; WO2010/123956; (2010); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

939-80-0, name is 4-Chloro-3-nitrobenzonitrile, 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. 939-80-0

Example 224 Preparation of 6-L-CYCLOHEXYL-5- (1H-TETRAZOL-5-YL)-1H-BENZIMIDAZOL-2-VLL-2- PHENYLQUINOXALINE (Compound 258) Step 1: 4-CYCLOHEXYLAMINO-3-NITROBENZONITRILE (Compound 127); [0776] A solution of 1 g (5.48 mmol) 4-CHLORO-3-NITROBENZONITRILE, Compound 126, and 1.14 g (11. 51 mmol) of cyclohexylamine were heated overnight in 5 mL anhydrous DMF. After cooling to room temperature, the solution was added dropwise into 100 mL H20 stirring vigorously. The solids were collected by filtration and dried under vacuum yielding 1.34 g (100%) bright yellow solids which were used as such without analysis in the next step.

Statistics shows that 939-80-0 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-3-nitrobenzonitrile.

Reference:
Patent; GENELABS TECHNOLOGIES, INC; WO2005/12288; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A common compound: 939-80-0, name is 4-Chloro-3-nitrobenzonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 939-80-0

TO a mixture of 4-chloro-3-nitro-benzonitrile (24.0 g, 131 mmol) and 3,5-dichloro-phenol (32.0 g, 197 mmol) in dry THF (150 ml) was added NaH (6.84 g, 171 mmol) in portions and the mixture was refluxed for 1 hour. After cooled to room temperature, the solvent was evaporated, and 100 ml of ice water and 20 ml of 4N NAOH aq. were added to the residue. The precipitate was collected by filtration, washed with 0.5 N NAOH aq. and water, dried in vacuo to give the 5-cyano-2- (3, 5-dichlorophenoxy) nitrobenzene (40.0 g, 98.4%) as slight yellow solid.

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, 939-80-0, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER HEALTHCARE AG; WO2004/84898; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

939-80-0, A common compound: 939-80-0, name is 4-Chloro-3-nitrobenzonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Step 5 4-(Cyclohexylcarbamoylmethylamino)-3-nitrobenzonitrile Cyclohexylcarbamoylmethylcarbamic acid benzyl ester (16.359 g) was hydrogenated using 7.5% palladium carbon (3.24 g) in ethanol (164 ml) solution at atmospheric pressure over 8 hours. After completion of the reaction, the reaction mixture was filtered through celite, and the solvent was evaporated. The obtained residue was dissolved in a mixture of ethanol (50 ml) and isopropanol (50 ml). Thereto were added 4-chloro-3-nitrobenzonitrile (8.23 g) and triethylamine (7.1 ml), and the stirred under reflux for 6 hours. After completion of the reaction, water was added under reflux and the mixture was ice-cooled. The resultant solid was collected by filtration and washed successively with water and diisopropyl ether to give the title compound (10.211 g). 1H-NMR (delta ppm, CDCl3) 1.13 (m, 3H), 1.38 (m, 2H), 1.70 (m, 3H), 1.91 (m, 2H), 3.84 (m, 1H), 4.01 (d, J=5.4 Hz, 2H), 5.76 (brd, 1H), 6.81 (d, J=8.7 Hz, 1H), 7.65 (dd, J=2.1, 8.7 Hz, 1H), 8.54 (d, J=2.1 Hz, 1H), 8.81 (brtr, 1H).

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-Chloro-3-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Japan Tobacco Inc.; US6562828; (2003); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

939-80-0, A common compound: 939-80-0, name is 4-Chloro-3-nitrobenzonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

4-Chloro-3-nitro-benzonitrile (30 g, 165 mmol) was suspended in EtOH (60 mL), and methylamine (33% in EtOH, 24 ml, 165 mmol) was added. The mixture was stirred at room temperature for 1 h, then heated to 7O0C overnight. The reaction mixture was cooled to rt and concentrated in vacuo. The residue was suspended in Et2O and filtered to give 42 g of 4- methylamino-3-nitro-benzonitrile, which was used in the next step without further purification. 400 MHz 1H NMR (CD3OD) delta (ppm): 8.5 (s, 1 H), 7.70 (d, J = 9 Hz, 1H), 7.09 (d, J = 9 Hz, 1H), 3.29 (s, 3H); APCI” MS+ 177.

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-Chloro-3-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/12623; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

939-80-0, 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. 939-80-0 name is 4-Chloro-3-nitrobenzonitrile, 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 158(1)3-Amino-4-{4-iodo-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl}benzonitrile (158a)Compound (153a) (5.00 g), cesium carbonate (6.72 g), and 4-chloro-3-nitrobenzonitrile (3.21 g) were suspended in acetonitrile (50 mL), followed by stirring at 70 C. for 4 hr. A saturated aqueous ammonium chloride solution was added to the reaction solution, and the precipitate was collected by filtration and dried under reduced pressure to obtain 4-{4-iodo-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-3-nitrobenzonitrile (7.19 g, 98%). The obtained 4-{4-iodo-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-3-nitrobenzonitrile (7.19 g) was suspended in THF (50 mL), MeOH (50 mL), and water (50 mL), and ammonium chloride (7.20 g) and iron powder (8.76 g) were added to the resulting suspension, followed by stirring at 80 C. for 2 hr. The reaction solution was diluted with ethyl acetate, and insoluble matters were filtered by celite. The solvent of the filtrate was distilled away, and water was added to the residue. Insoluble matters were collected by filtration and dried under reduced pressure to obtain compound (158a) (6.44 g, 96%).1H-NMR (DMSO-d6) delta: 8.26 (1H, d, J=4.63 Hz), 8.08 (1H, d, J=4.63 Hz), 7.42 (1H, d, J=8.05 Hz), 7.23 (1H, s), 7.04 (1H, d, J=8.05 Hz), 5.80 (2H, s); LRMS (ESI) m/z 430 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Chloro-3-nitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; TAIHO PHARMACEUTICAL CO., LTD.; US2012/108589; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 939-80-0, name is 4-Chloro-3-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 939-80-0

In a flask equipped with a reflux condenser, frans-4-aminocyclohexanol hydrochloride(2.70g, 17.80mmoles) was suspended in iso-propanol (15m1). To this stirred suspension,triethylamine (4,40m1, 31 .49mmoles) was slowly added, followed by 4-chloro-3- nitrobenzonitrile (2.50g, 13.69mmoles). The resulting yellow suspension was heated at 65C for 36h, allowed to cool down to room temperature before water (lOml) was added to the reaction mixture. The resulting precipitate was collected by filtration andsuccessively washed with water and iso-propanol, to yield 4-(((1R,4R)-4- hydroxycyclohexyl)amino)-3-nitrobenzonitrile as a yellow crystalline solid (3 .28g, 12.55mmoles, 92%). The resulting solid was further purified by recrystallization from hot ethanol.mlz 262.2 [MJ-1]+?H NMR (500 MHz, DMSO-d6) oe 8.49 (s, 1H), 8.18 (d, J = 7.8 Hz, 1H), 7.79 (d, J = 9.0 Hz, 1H), 7.26 (d, J = 9.1 Hz, 1H), 4.63 (s, 1H), 3.67 (dtd, J = 14.9, 10.4, 4.0 Hz, 1H), 3.57-3.41 (m, 1H), 2.05-1.88 (m, 2H), 1.89-1.75 (m,2H), 1.53-1.19 (m, 4H).

The synthetic route of 939-80-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RE:VIRAL LTD; COCKERILL, Stuart; MATHEWS, Neil; WARD, Simon; LUNN, Graham; PARADOWSKI, Michael; GASCON SIMORTE, Jose Miguel; (72 pag.)WO2016/55780; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts