14 Sep 2021 News Analyzing the synthesis route of 6332-56-5

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Application of 6332-56-5, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.6332-56-5, name is 3-Nitropyridin-2(1H)-one, molecular formula is C5H4N2O3, molecular weight is 140.1, as common compound, the synthetic route is as follows.

a)Preparation of 2-amino-3-hydroxypyridine To a solution of 2-hydroxy-3-nitropyridine (5 g, 45.4 mmol) in methanol(250 ml) was added 10% Pd/C (1 g). The mixture was flushed with argon, then hydrogen was bubbled through the solution for 10 min. and a hydrogen atmosphere was maintained at balloon pressure overnight. The mixture was filtered through celite and the celite was washed with methanol. The solvent was evaporated and chromatography of the resulting solid on silica gel (5% MeOH/CH2Cl2) gave the desired product(3.2 g, 89%). 1H NMR (CD3OD): delta 6.96 (d, 1H), 6.90 (dd, 1H), 6.77 (d, 1H).

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Reference:
Patent; SmithKline Beecham Corporation; US6218539; (2001); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Some scientific research about 3-Nitropyridin-2(1H)-one

The synthetic route of 6332-56-5 has been constantly updated, and we look forward to future research findings.

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a. 5-bromo-3-nitro-pyridine-2-ol-hydrobromide 3.6 ml of bromine are added dropwise to a suspension of 10.0 g (0.071 mol) of 2-hydroxy-3-nitro-pyridine in 25 ml of carbon tetrachloride whilst cooling with ice. The reaction mixture is refluxed for 2 hours. The solvent is distilled off in vacuo, the crystalline product is suction filtered and recrystallized from water. Yield: 7.5 g (35.1% of theory).

The synthetic route of 6332-56-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim Pharma KG; US6200976; (2001); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

New learning discoveries about 3-Nitropyridin-2(1H)-one

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Reference of 6332-56-5, 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. 6332-56-5, name is 3-Nitropyridin-2(1H)-one. A new synthetic method of this compound is introduced below.

2-Hydroxy-3-nitro-pyridine (75 g, 0.535 mole) and 1400 ML of anhydrous tetrahydrofuran were stirred at 0 C. using a mechanical stirrer.. lithium bis(trimethylsilyl)amide (1.0 M solution in tetrahydrofuran, 683.5 ML) was slowly added over 30 minutes.. The deep brown reaction mixture was stirred for 30 additional minutes and then t-butyl bromoacetate (109.6 g, 0.561 mole) was slowly added over 30 minutes.. The reaction mixture was warmed to 25 C. overnight.. The organic solvents were removed under vacuum and the residue was dissolved in 2 liters of ethyl acetate and 500 ML of water.. The organic phase was dried with magnesium sulfate, filtered and evaporated under vacuum.. The residue was chromatographed on silica gel using a methylene chloride:ethanol gradient, 100:0 to 98:2, to yield 102.1 g (75 %) of the title compound as a yellow-orange solid.

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Reference:
Patent; Corvas International, Inc.; US6342504; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Sources of common compounds: 6332-56-5

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2-Oxo-3-nitro-N-(carbomethoxymethyl)-pyridinone (109). 2-Hydroxy-3-nitropyridine 108 (10 g, 71.38 mmole) is mixed with pulverized potassium carbonate (10.9 g, 78.5 mmole) and 30 mL of DMF. After 10 min, methyl bromoacetate (10.4 mL, 107 mmole) is added. The resulting mixture is stirred at room temperature for 4.5 hr. The reaction is quenched by water and extracted by ethyl acetate. The organic layer is then washed with brine, dried over MgSO4, filtered and evaporated to give an oil which is chromatographed over flash silica with EtOAc to give 109.

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Reference:
Patent; The Procter & Gamble Company; US5672598; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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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. 6332-56-5, name is 3-Nitropyridin-2(1H)-one. A new synthetic method of this compound is introduced below., Recommanded Product: 3-Nitropyridin-2(1H)-one

Example 97A methyl 4-(3-nitro-2-oxopyridin-1(2H)-yl)benzoate A mixture of 2-hydroxy-3-nitropyridine (1.168 g, 8.33 mmol), copper (II) acetate (2.271 g, 12.50 mmol), 4-methoxycarbonylphenylboronic acid (3 g, 16.67 mmol) and pyridine (10.11 mL, 125 mmol) was stirred under N2 for 5 minutes, and the atmosphere (balloon) was changed to O2. The mixture was then stirred at 90 C. overnight. The mixture was cooled to room temperature, treated with water (50 mL) and stirred for 5 minutes. The solid was collected by filtration, washed with water, and dried under vacuum. The solid was chromatographed on silica gel eluting with a gradient of 0-100% ethyl acetate in [9:1 CH2Cl2:ethyl acetate] to provide the title compound (1.57 g, 5.73 mmol, 68.7% yield). 1H NMR (400 MHz, DMSO-d6) delta 8.53 (dd, J=7.7, 2.0 Hz, 1H), 8.20 (dd, J=6.7, 2.0 Hz, 1H), 8.12 (d, J=8.5 Hz, 2H), 7.67 (d, J=8.5 Hz, 2H), 6.58-6.53 (m, 1H), 3.90 (s, 3H); MS (ESI+) m/z 275 (M+H)+.

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, 6332-56-5, 3-Nitropyridin-2(1H)-one.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Cowart, Marlon D.; Esmieu, William Ramesh; Gfesser, Gregory A.; Greszler, Stephen N.; Koenig, John R.; Kym, Philip R.; Liu, Bo; Malagu, Karine Fabienne; Patel, Sachin V.; Scanio, Marc J.; Searle, Xenia B.; Voight, Eric; Wang, Xeuqing; Yeung, Ming C.; (202 pag.)US2017/15675; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Analyzing the synthesis route of 6332-56-5

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Adding a certain compound to certain chemical reactions, such as: 6332-56-5, 3-Nitropyridin-2(1H)-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, Safety of 3-Nitropyridin-2(1H)-one, blongs to pyridine-derivatives compound. Safety of 3-Nitropyridin-2(1H)-one

(1a-1) To a solution of 2-hydroxy-3-nitropyridine (Aldrich, 3.0 mmol, 420 mg) in 1,4-dioxane (20 mL), were added 4-fluorophenyl boronic acid (Combi-block, 6.0 mmol, 840 mg), copper(II) acetate (Aldrich, 4.5 mmol, 815 mg) and pyridine (2 mL). The reaction was heated at 80 C. for 20 h. After cooling to room temperature, 30 mL of cold water was added. The solid formed was collected by filtration, washed with ammonium hydroxide and water, and dried under vacuum to give 1-(4-fluorophenyl)-3-nitropyridin-2(1H)-one (610 mg, 87% yield) as a solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6332-56-5, 3-Nitropyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/78136; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The origin of a common compound about Reference of 6332-56-5

Statistics shows that 6332-56-5 is playing an increasingly important role. we look forward to future research findings about 3-Nitropyridin-2(1H)-one.

Reference of 6332-56-5, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.6332-56-5, name is 3-Nitropyridin-2(1H)-one, molecular formula is C5H4N2O3, molecular weight is 140.1, as common compound, the synthetic route is as follows.

(14a) 3-Nitro-1-phenyl-1,2-dihydropyridin-2-one 5g of 2-hydroxy-3-nitropyridine, 7.14g of phenylboronic acid, 2.6g of copper (II) acetate, 9.9ml of triethylamine and 5.8ml of pyridine were added to 100ml of tetrahydrofuran, followed by stirring overnight. The reaction mixture was poured into aqueous ammonia, and extracted with ethyl acetate. The organic layer was washed with water, dried, and concentrated. The residue was suspended into ether, and collected by filtration, to give 4.71g of the title compound. 1H-NMR (400MHz, CDCl3); delta(ppm) 6.39(dd, 1H), 7.36-7.40(m, 2H), 7.49-7.54(m, 3H), 7.73(dd, 1H), 8.38(dd, 1H).

Statistics shows that 6332-56-5 is playing an increasingly important role. we look forward to future research findings about 3-Nitropyridin-2(1H)-one.

Reference:
Patent; Eisai Co., Ltd.; EP1300396; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem