Category: 14150-94-8

Adding a certain compound to certain chemical reactions, such as: 14150-94-8, 1-Methyl-3,5-dinitro-1H-pyridin-2-one, 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, HPLC of Formula: C6H5N3O5, blongs to pyridine-derivatives compound. HPLC of Formula: C6H5N3O5

11.2 (3-Nitro-5,6,7,8-tetrahydro-quinolin-5 and 7-yl)-carbamic acid benzyl ester; A mixture of 1-methyl-3,5-dinitro-2-pyridone (3.66 g, 18.38 mmol) and (3-oxo- cyclohexyl)-carbamic acid benzyl ester (4.55 g, 18.39 mmol) in methanolic am¬ monia (1 M1 140 ml) was heated at 65C for 1.5 h. It was then concentrated and digested in CH2CI2. The organic layer was washed with H2O (x2), dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel (heptane:ethyl acetate, 3:1) to afford a mixture 1/2 of the 5 and 7 regioisomers (4.51 g, 75% for two steps) as a pale yellow gum. MS (ESI+) m/z = 328.1 [M+H]+ 1H NMR (400 MHz, CDCI3) : delta (ppm) 1.83 (m, 1.5H), 2.01 (m, 1H), 2.20 (m, 1.5H), 2.90 (dd, J = 18.1 , 8.7 Hz1 1H), 3.00 (t, J = 6.4 Hz1 2H), 3.05 (t, J = 6.4 Hz, 1 H)13.43 (dd, J = 18.1 , 5.2 Hz1 1H)1 4.16 (m, 1H)1 4.81 (bs, 1 H)1 5.03 (bs, 1H), 5.12 (s, 2H), 5.19 (s, 1 H), 7.36 (m, 7.5 H)1 8.19 (bs, 1H), 8.46 (bs, 0.5H)1 9.20 (d, J = 1.9 Hz, 1 H), 9.23 (d, J = 2.1 Hz1 0.5H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14150-94-8, 1-Methyl-3,5-dinitro-1H-pyridin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; ABBOTT GMBH & CO.KG; WO2006/40178; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14150-94-8, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 14150-94-8, name is 1-Methyl-3,5-dinitro-1H-pyridin-2-one. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of (+/-)- 1 ‘- { [2-(trimethylsilyl)ethoxy]methyl} -3H-spiro[cyclopentane- l,3′-pyrrolo[2,3-]pyridine]-2’,3(l’H)-dione from Step A (230 mg, 0.692 mmol) and 1-methyl- 3,5-dinitropyridin-2(lH)-one (173 mg, 0.869 mmol) [Tohda et al. (1990) Bull. Chem. Soc. Japan 63, 2820] in 2 M ammonia in MeOH (3.5 mL) was heated to reflux for 18 h. The mixture was concentrated in vacuo and purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc – 100:0 to 50:50, to give the title compound. MS: mlz = 413 (M + 1).

According to the analysis of related databases, 14150-94-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2008/73251; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 14150-94-8, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 14150-94-8, name is 1-Methyl-3,5-dinitro-1H-pyridin-2-one. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of the dinitropyridone 1 (50 mg, 0.25 mmol) in ethanol (10 mL), 4-phenyl-3-buten-2-one (4a) (36.5 mg, 0.25 mmol) and NH4OAc (578 mg, 7.5 mmol) were added, and the resultant mixture was heated at 65 C for 24 h. After removal of the solvent, the residue was washed with benzene (3 × 10 mL) to remove unreacted ketone 4a and treated with column chromatography on silica gel (eluent: hexane/ethyl acetate =95/5) to afford 5-nitro-2-(2-phenylethenyl)pyridine (5a) (41 mg, 0.18 mmol, 72%) as a yellow powder. The reactions of the dinitropyridone 1 with other ketones 4b-f or 10a-c were performed in a similar way.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 14150-94-8, 1-Methyl-3,5-dinitro-1H-pyridin-2-one.

Reference:
Article; Le, Song Thi; Asahara, Haruyasu; Nishiwaki, Nagatoshi; Chemistry Letters; vol. 44; 6; (2015); p. 776 – 778;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 14150-94-8, name is 1-Methyl-3,5-dinitro-1H-pyridin-2-one. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 1-Methyl-3,5-dinitro-1H-pyridin-2-one

Into a 50 mL sealed tube was placed tert-butyl 3-methyl-4-oxocyclohexane-1-carboxylate (2.7 g, 14.7 mmol) and 1-methyl-3,5-dinitro-1,2-dihydropyridin-2-one (2.9 g, 14.7 mmol). Added 7M ammonia in methanol (20 mL), sealed, and stirred overnight at 100 C. The mixture was cooled and concentrated. The crude product was purified by preparatory HPLC. Pure fractions were combined and concentrated to yield the title compound (1.7 g, 49%) as an oil.

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, 14150-94-8, 1-Methyl-3,5-dinitro-1H-pyridin-2-one.

Reference:
Patent; LYCERA CORPORATION; AICHER, Thomas Daniel; SKALITZKY, Donald J.; TOOGOOD, Peter L.; VANHUIS, Chad A.; (416 pag.)WO2019/200120; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 14150-94-8 , The common heterocyclic compound, 14150-94-8, name is 1-Methyl-3,5-dinitro-1H-pyridin-2-one, molecular formula is C6H5N3O5, 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.

A mixture of SP-0010418-2 (1.2 g, 5.128 mmol), 1-methyl-3,5-dinitropyridin- 2(1H)-one (1.53 g, 7.692 mmol) and 7.0 M NH3/MeOH (2.0 mL) in MeOH (8.0 mL) was stirred at 90 C for 0.5 h under microwave irridation. The residue was purified by silica gel column chromatography (using petroleum ether/EtOAc = 10:0 – 7:3) to give mixture SP0010418-162-3A and SP-0010418-162-3B (910 mg, yield: 57%). LC-MS 314 (M+H), 91%(UV2l4nm).

The synthetic route of 14150-94-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; F.HOFFMANN-LAROCHE LTD; YUAN, Junying; HAN, Nianhe; YI, Hua; WANG, Yuguang; YANG, Song; WONG, Jason, Christopher; WO2014/145512; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 14150-94-8, name is 1-Methyl-3,5-dinitro-1H-pyridin-2-one. A new synthetic method of this compound is introduced below., Recommanded Product: 14150-94-8

General procedure: To a solution of the dinitropyridone 1 (50 mg, 0.25 mmol) in ethanol (10 mL), 4-phenyl-3-buten-2-one (4a) (36.5 mg, 0.25 mmol) and NH4OAc (578 mg, 7.5 mmol) were added, and the resultant mixture was heated at 65 C for 24 h. After removal of the solvent, the residue was washed with benzene (3 × 10 mL) to remove unreacted ketone 4a and treated with column chromatography on silica gel (eluent: hexane/ethyl acetate =95/5) to afford 5-nitro-2-(2-phenylethenyl)pyridine (5a) (41 mg, 0.18 mmol, 72%) as a yellow powder. The reactions of the dinitropyridone 1 with other ketones 4b-f or 10a-c were performed in a similar way.

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, 14150-94-8, 1-Methyl-3,5-dinitro-1H-pyridin-2-one.

Reference:
Article; Le, Song Thi; Asahara, Haruyasu; Nishiwaki, Nagatoshi; Chemistry Letters; vol. 44; 6; (2015); p. 776 – 778;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14150-94-8, Adding some certain compound to certain chemical reactions, such as: 14150-94-8, name is 1-Methyl-3,5-dinitro-1H-pyridin-2-one,molecular formula is C6H5N3O5, 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 14150-94-8.

A mixture ofbenzyl (3-oxocyclohexyl)carbamate (247 mg, 0.999 mmol) and 1-methyl- 3,5-dinitropyridin-2(1H)-one (300 mg, 1.507 mmol) in ammonia/MeOH (1M, 6 mL) was microwaved at 90 C for 30 mm to provide a blackish-red solution. Eleven more samples of the same composition were run under the same conditions. The twelve samples were combined and evaporated under reduced pressure. The residue was partitioned between DCM (300 mL) and saturated aqueous NaHCO3 (100 mL). The organic layer was washed with brine (100 mL), dried (MgSO4), filtered, treated with silica gel, and evaporated under reduced pressure. Purification by silica gel chromatography (0 to 50% EtOAc in hexanes) provided a mixture of benzyl (3-nitro- 5,6,7, 8-tetrahydroquinolin-7-yl)carbamate and undesired regioi somer benzyl (3 -nitro-5 ,6,7, 8-tetrahydroquinolin-5-yl)carbamate as a pale yellow gum. The mixture was used without further purification. MS (ESI, m/z): 213 [M+H]t; j00424J A solution of benzyl (3 -nitro-5 ,6,7, 8-tetrahydroquinolin-7-yl)carbamate and regioisomer (2.64 g, 8.07 mmol) in ethanol (110 mL) was treated with tin(II) chloride dihydrate (9.10 g, 40.3 mmol) and conc. HC1 (1 mL), then stirred at 80 C for 75 mm. The solution was allowed to cool, then was concentrated under reduced pressure to about 15 mL. The sample was made basic (pH 9) by addition of saturated aqueous NaHCO3; about midway through, the sample was diluted with DCM (100 mL). The mixture was triturated, then filtered, and the filter cake was washed with DCM (50 mL). The filter cake was triturated and sonicated in MeOH (200 mL), then the mixture was filtered. The slightly cloudy filtrate was filtered through Celite 545, then concentrated to provide a yellow solid. Purification by silica gel chromatography (0 to 15% MeOH in DCM) provided a mixture of benzyl (3-amino-5,6,7,8-tetrahydroquinolin-7-yl)carbamate and regioisomer as a yellow solid. The mixture was used without further purification. MS (ESI, m/z):298 [M+H]t; 1004251 A sample of benzyl (3-amino-S ,6, 7, 8-tetrahydroquinolin-7-yl)carbamate and regioisomer (1.25 g, 4.22 mmol) was treated with ACN (17 mL). The material was cooled on a dry ice / ethylene glycol bath (approximately -10 to -15 C) and PTSA monohydrate (1.61 g, 8.45 mmol) was added. After stirring 10 mm, a solution of potassium iodide (1.05 g, 6.33 mmol) and sodium nitrite (0.436 g, 6.32 mmol) in water (3.4 mL) was added dropwise over 20 mm. The dry ice bath was replaced with an ice bath, and the reddish-brown mixture was stirred at 0 C for 3 h 40 mm. The solution was diluted with EtOAc (50 mL), cooled on an ice bath and treated with saturated aqueous NaHCO3 until basic (pH 8-9). The organic layer was removed and the aqueous layer was extracted once more with EtOAc (50 mL). The combined organics were washed sequentially with water and brine (50 mL each), dried (Na2504), filtered, treated with silica gel, and evaporated under reduced pressure. Purification by silica gel chromatography (0 to 23% EtOAc in hexanes) provided a mixture of benzyl (3-iodo-S,6,7,8-tetrahydroquinolin-7- yl)carbamate and regioisomer as a yellow solid. The mixture was used without further purification.MS (ESI, m/z): 409 [M+H]; 1004261 A mixture of t-BuXPhos Pd G4 (76.3 mg, 94.4 tmole), benzyl (3-iodo-5,6,7,8- tetrahydroquinolin-7-yl)carbamate and regioisomer (605.0 mg, 1.482 mmol), tert-butyl piperazine-1-carboxylate (553.5 mg, 2.97 mmol), and sodium tert-butoxide (257.1 mg, 2.68 mmol) was sealed in a 40-mL vial. The atmosphere was evacuated and replaced with nitrogen, three times. Dioxane (15 mL) was added and the solution was stirred at ambient temperature for three days. Material at the same stage from a previous run (from 40.7 mg, 0.100 mmol iodo starting material) was added. The mixture was diluted with EtOAc (100 mL), treated with silica gel, and evaporated under reduced pressure. Purification by silica gel chromatography (0 to 87% EtOAc in hexanes) provided a mixture of tert-butyl 4-(7-(((benzyloxy)carbonyl)amino)-5 ,6,7, 8-tetrahydroquinolin-3 – yl)piperazine-1-carboxylate and regioisomer as a yellow foam. The mixture was used without further purification. MS (ESI, m/z): 467 [M+H].

According to the analysis of related databases, 14150-94-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZABLOCKI, Mary-Margaret; GUERIN, David J.; NG, Pui Yee; WANG, Zhongguo; SHELEKHIN, Tatiana; CARAVELLA, Justin; LI, Hongbin; IOANNIDIS, Stephanos; (518 pag.)WO2019/32863; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 14150-94-8, 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 14150-94-8 as follows.

To a solution of 1-methyl-3,5-dinitro-2-pyridone (8.0 g, 40 mmol) in methyl alcohol (20 mL) was added dropwise 3-methyl-2-butanone (5.1 mL, 48 mmol), followed by ammonia solution in methyl alcohol (10.0 g, 17%, 100 mmol). The reaction mixture was heated at 70 C. for 2.5 h under atmospheric pressure. The solvent was removed under vacuum and the residual oil was dissolved in CH2Cl2, and then filtered. The filtrate was dried over Na2SO4 and concentrated to afford 2-isopropyl-5-nitro-pyridine (1.88 g, 28%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14150-94-8, its application will become more common.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Van Goor, Fredrick F.; Burton, William Lawrence; US2015/231142; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 14150-94-8, name is 1-Methyl-3,5-dinitro-1H-pyridin-2-one. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H5N3O5

A mixture ofbenzyl (3-oxocyclohexyl)carbamate (247 mg, 0.999 mmol) and 1-methyl- 3,5-dinitropyridin-2(1H)-one (300 mg, 1.507 mmol) in ammonia/MeOH (1M, 6 mL) was microwaved at 90 C for 30 mm to provide a blackish-red solution. Eleven more samples of the same composition were run under the same conditions. The twelve samples were combined and evaporated under reduced pressure. The residue was partitioned between DCM (300 mL) and saturated aqueous NaHCO3 (100 mL). The organic layer was washed with brine (100 mL), dried (MgSO4), filtered, treated with silica gel, and evaporated under reduced pressure. Purification by silica gel chromatography (0 to 50% EtOAc in hexanes) provided a mixture of benzyl (3-nitro- 5,6,7, 8-tetrahydroquinolin-7-yl)carbamate and undesired regioi somer benzyl (3 -nitro-5 ,6,7, 8-tetrahydroquinolin-5-yl)carbamate as a pale yellow gum. The mixture was used without further purification. MS (ESI, m/z): 213 [M+H]t; j00424J A solution of benzyl (3 -nitro-5 ,6,7, 8-tetrahydroquinolin-7-yl)carbamate and regioisomer (2.64 g, 8.07 mmol) in ethanol (110 mL) was treated with tin(II) chloride dihydrate (9.10 g, 40.3 mmol) and conc. HC1 (1 mL), then stirred at 80 C for 75 mm. The solution was allowed to cool, then was concentrated under reduced pressure to about 15 mL. The sample was made basic (pH 9) by addition of saturated aqueous NaHCO3; about midway through, the sample was diluted with DCM (100 mL). The mixture was triturated, then filtered, and the filter cake was washed with DCM (50 mL). The filter cake was triturated and sonicated in MeOH (200 mL), then the mixture was filtered. The slightly cloudy filtrate was filtered through Celite 545, then concentrated to provide a yellow solid. Purification by silica gel chromatography (0 to 15% MeOH in DCM) provided a mixture of benzyl (3-amino-5,6,7,8-tetrahydroquinolin-7-yl)carbamate and regioisomer as a yellow solid. The mixture was used without further purification. MS (ESI, m/z):298 [M+H]t; 1004251 A sample of benzyl (3-amino-S ,6, 7, 8-tetrahydroquinolin-7-yl)carbamate and regioisomer (1.25 g, 4.22 mmol) was treated with ACN (17 mL). The material was cooled on a dry ice / ethylene glycol bath (approximately -10 to -15 C) and PTSA monohydrate (1.61 g, 8.45 mmol) was added. After stirring 10 mm, a solution of potassium iodide (1.05 g, 6.33 mmol) and sodium nitrite (0.436 g, 6.32 mmol) in water (3.4 mL) was added dropwise over 20 mm. The dry ice bath was replaced with an ice bath, and the reddish-brown mixture was stirred at 0 C for 3 h 40 mm. The solution was diluted with EtOAc (50 mL), cooled on an ice bath and treated with saturated aqueous NaHCO3 until basic (pH 8-9). The organic layer was removed and the aqueous layer was extracted once more with EtOAc (50 mL). The combined organics were washed sequentially with water and brine (50 mL each), dried (Na2504), filtered, treated with silica gel, and evaporated under reduced pressure. Purification by silica gel chromatography (0 to 23% EtOAc in hexanes) provided a mixture of benzyl (3-iodo-S,6,7,8-tetrahydroquinolin-7- yl)carbamate and regioisomer as a yellow solid. The mixture was used without further purification.MS (ESI, m/z): 409 [M+H]; 1004261 A mixture of t-BuXPhos Pd G4 (76.3 mg, 94.4 tmole), benzyl (3-iodo-5,6,7,8- tetrahydroquinolin-7-yl)carbamate and regioisomer (605.0 mg, 1.482 mmol), tert-butyl piperazine-1-carboxylate (553.5 mg, 2.97 mmol), and sodium tert-butoxide (257.1 mg, 2.68 mmol) was sealed in a 40-mL vial. The atmosphere was evacuated and replaced with nitrogen, three times. Dioxane (15 mL) was added and the solution was stirred at ambient temperature for three days. Material at the same stage from a previous run (from 40.7 mg, 0.100 mmol iodo starting material) was added. The mixture was diluted with EtOAc (100 mL), treated with silica gel, and evaporated under reduced pressure. Purification by silica gel chromatography (0 to 87% EtOAc in hexanes) provided a mixture of tert-butyl 4-(7-(((benzyloxy)carbonyl)amino)-5 ,6,7, 8-tetrahydroquinolin-3 – yl)piperazine-1-carboxylate and regioisomer as a yellow foam. The mixture was used without further purification. MS (ESI, m/z): 467 [M+H]; 1004271 A suspension of Pd/C (10%) (57.1 mg, 0.054 mmol) and the mixture of tert-butyl 4-(7- (((benzyloxy)carbonyl)amino)-5 ,6, 7, 8-tetrahydroquinolin-3 -yl)piperazine- 1 -carboxylate and regioisomer (485 mg, 1.039 mmol) in MeOH (5 mL) was stirred at ambient temperature under an atmosphere of hydrogen overnight. The sample was filtered through Celite 545 under vacuum, and the Celite was rinsed with MeOH. The filtrate was evaporated to provide a mixture of tert-butyl 4- (7-amino-S ,6, 7, 8-tetrahydroquinolin-3 -yl)piperazine- 1 -carboxylate and regioi somer as an orange gum. The mixture was used without further purification. MS (ESI, m/z): 333 [M+H]t; j00428J A solution of tert-butyl 4-(7-amino-S ,6,7, 8-tetrahydroquinolin-3 -yl)piperazine- 1- carboxylate and regioisomer (130 mg, 0.391 mmol) in DCM …

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, 14150-94-8, 1-Methyl-3,5-dinitro-1H-pyridin-2-one.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZABLOCKI, Mary-Margaret; GUERIN, David J.; NG, Pui Yee; WANG, Zhongguo; SHELEKHIN, Tatiana; CARAVELLA, Justin; LI, Hongbin; IOANNIDIS, Stephanos; (518 pag.)WO2019/32863; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 14150-94-8 , The common heterocyclic compound, 14150-94-8, name is 1-Methyl-3,5-dinitro-1H-pyridin-2-one, molecular formula is C6H5N3O5, 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: To a solution of dinitropyridone 1 (50.0 mg, 0.25 mmol) in ethanol (5 ml), were added enaminone 4a (38.8 mg, 0.25 mmol) and triethylamine (35mul, 0.25 mmol). The resultant mixture was heated at 100 C for 1 day. After evaporation, the residue was treated with column chromatography on alumina to afford 2-ethanoly-4-nitro-N-propylaniline (3a) (eluted with hexane/ethyl acetate = 8/2, 23.0 mg, 0.11 mmol, 43% (NMR Yield 63%)) as a yellow solid.

The synthetic route of 14150-94-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Naito, Saki; Yokoyama, Soichi; Asahara, Haruyasu; Nishiwaki, Nagatoshi; Tetrahedron Letters; vol. 58; 50; (2017); p. 4699 – 4702;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem