Tag: M.W:100-200

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. 4966-90-9, name is 4-Hydroxy-6-methyl-3-nitropyridin-2(1H)-one, molecular formula is C6H6N2O4, The 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. Recommanded Product: 4-Hydroxy-6-methyl-3-nitropyridin-2(1H)-one

Part A A mixture of 6-methyl-3-nitropyridine-2,4-diol (50 g, 0.29 mol) and phosphorus oxychloride (500 mL) was heated at 90 C. overnight. The excess phosphorus oxychloride was removed under reduced pressure. The resulting black oil was poured into water (1.8 L) and ice. This mixture was extracted with chloroform (*8, 3 L total) and filtered to remove black particulates and break up an emulsion. The combined organics were washed with 10% sodium carbonate (*2) and brine, dried and then concentrated under reduced pressure to provide 52 g of an amber oil. This oil was recrystallized from heptane (115 mL) to provide 43.5 g of 2,4-dichloro-6-methyl-3-nitropyridine as large amber crystals.

With the rapid development of chemical substances, we look forward to future research findings about 4966-90-9.

Reference:
Patent; 3M Innovative Properties Company; US6545017; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 19230-59-2 , The common heterocyclic compound, 19230-59-2, name is 2-Methoxy-3-methylpyridine, molecular formula is C7H9NO, 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.

(lb) 2-Methoxy-3-methyl-5-nitropyridine [Formula 9]; Concentrated sulfuric acid (5 ml) and fuming nitric acid (5 ml) were added to 2-methoxy-3- methylpyridine (1.61 g, 13.1 mmol) under ice cooling, and stirred at 0C for 1 hour and further stirred at room temperature overnight. The reaction mixture was poured onto ice, neutralized with ammonia solution, extracted with ethyl acetate, dried over magnesium sulfate, the solvent was evaporated, thereby yielding the title compound (1.63 g, 9.71 mmol, and 74%). ¹H NMR(400MHz, DMSO-d6) 8 ppm; 2.25(3H, s), 4.04(3H, s), 8.37-8.40(lH, m), 8.92-8.95 (1H, m).

The synthetic route of 19230-59-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EISAI CO., LTD.; WO2005/103049; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 75711-01-2, 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 75711-01-2, name is 6-Chloro-5-methoxypyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows.

To an ice-cooled suspension of 6-chloro-5-(methyloxy)-3-pyridinamine D46 (2.14 g, 13.50 mmol) in HCl 4 M in water (10.12 ml, 40.50 mmol), a solution of sodium nitrite (1.02 g, 14.84 mmol) in water (7 ml) was added dropwise over a 5 min period and the resulting mixture was vigorously stirred at 5 C. for 30 min. To the mixture at 5 C. was added a solution of NaBF4 (2.67 g, 24.29 mmol) in water (17 ml). The thick suspension was collected by filtration, washed with cold water and a little amount of cold EtOH and dried under reduced pressure at 55 C. for 8 h. The resulting black solid was taken-up in xylenes (25 ml) and allowed to reflux for 1 h. The solvent was evaporated under reduced pressure, the residue dissolved in EtOAc and washed with a saturated NaHCO3 aqueous solution. The organic phase was separated, dried (Na2SO4), filtered and the solvent removed under vacuum. The resulting black oil was purified by flash chromatography on silica gel (Biotage SP4 25M, Cy/EtOAc 95/5) to afford the title compound D47 (0.11 g, 0.69 mmol, 5% yield) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) delta (ppm): 8.03 (d, 1H), 7.70 (dd, 1H), 3.92 (s, 3H).

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 75711-01-2, 6-Chloro-5-methoxypyridin-3-amine.

Reference:
Patent; ALVARO, GIUSEPPE; AMANTINI, DAVID; BELVEDERE, SANDRO; US2009/22670; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 403-45-2 ,Some common heterocyclic compound, 403-45-2, molecular formula is C6H4FNO2, 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.

Methyl 6-fluoronicotinate. To a solution of 6-fluoronicotinic acid (255 mg, 1.32 mmol) in methanol (5 mL) at room temperature was added (trimethylsilyl)diazomethane (4.0 mL, 2 M in diethyl ether, 8.0 mmol). The reaction mixture was stirred at room temperature for 30 min and concentrated. Methyl 6- fluoronicotinate (129 mg, 47%) was used without further purification: 1H NMR (600 MHz, DMSOd6) delta 8.79 (d, J = 2.6 Hz, IH), 8.47 (td, J = 7.9, 2.6 Hz, IH), 7.35 (ddd, J = 8.5, 2.6, 0.6 Hz, IH), 3.88 (s, 3H); ESIMS calcd 156.0 (M+ + H), found 156.1 (M+ + H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,403-45-2, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; ATON PHARMA, INC.; WO2007/2248; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1122-43-6, 2,6-Dimethyl-3-hydroxypyridine, 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, 1122-43-6, blongs to pyridine-derivatives compound. Product Details of 1122-43-6

Step A: 2,6-Dimethylpyridin-3-ol (1.0 g, 8.1 mmol) was dissolved in aqueous NaOH (4.05 mL, 2 M, 8.1 mmol). To the solution was added iodine (2.62 g, 10.3 mmol) at room temperature. The mixture was stirred at 50 C. for 2 h, then neutralized (pH ?7) with aqueous HCl (2 N). Excess reagent was quenched with sodium thiosulfate, then the solvent was removed under vacuum. The residue was suspended in 10% MeOH in CH2Cl2 (100 mL) and filtered. The filtrate was concentrated to give 4-iodo-2,6-dimethylpyridin-3-ol (0.96 g, 50%). MS m/z 250.0 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1122-43-6, its application will become more common.

Reference:
Patent; PTC Therapeutics, Inc.; F. Hoffmann-La Roche AG; Woll, Matthew G.; Chen, Guangming; Choi, Soongyu; Dakka, Amal; Huang, Song; Karp, Gary Mitchell; Lee, Chang-Sun; Li, Chunshi; Narasimhan, Jana; Naryshkin, Nikolai; Paushkin, Sergey; Qi, Hongyan; Turpoff, Anthony A.; Weetall, Marla L.; Welch, Ellen; Yang, Tianle; Zhang, Nanjing; Zhang, Xiaoyan; Zhao, Xin; Pinard, Emmanuel; Ratni, Hasane; (317 pag.)US9617268; (2017); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 107867-51-6 , The common heterocyclic compound, 107867-51-6, name is 5-(Trifluoromethyl)pyridine-2,3-diamine, molecular formula is C6H6F3N3, 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 a stirred solution of 2-(6-bromopyridin-3-yl)-2-methoxyacetic acid (500 mg, 2.03 mmol) in pyridine(5 mL) was added 5 -(trifluoromethyl)pyridine-2,3 -diamine (396 mg, 2.23 mmol) and EDC (1.17 g, 6.10 mmol) at RT. After the addition was finished, the reaction was stirred at 40 C for 4 h. The solvent was removed in vacuo. The residue was diluted with water, extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2S04i filtered and concentrated in vacuo to afford a residue, which was purified by prep-TLC (petroleum ether : ethyl acetate =1 : 1) to give the title compound. MS (EI) m/z 405 [M+H]+.

The synthetic route of 107867-51-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ZHOU, Hua; FRADERA, Xavier; HAN, Yongxin; MCGOWAN, Meredeth, A.; SCIAMMETTA, Nunzio; WHITE, Catherine; YU, Wensheng; (89 pag.)WO2019/27856; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1122-61-8, 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 1122-61-8, name is 4-Nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Nitro compound (0.5 mmol), alcohol 1 (0.324 g, 1.75 mmol) and methyl acrylate (0.180 mL, 2 mmol) were mixed in toluene or acetonitrile (1 mL) degassed by several vacuum-nitrogen cycles to reduce the air oxidation of alcohol 1 to ketone 3. The resulting mixture was heated at 110 C in a screw-cap tube (Pyrex N. 15) until the disappearance of the starting nitro compound. Removal of the solvent in vacuo and purification by FC gave the beta-amino esters and ketone 3. The excess alcohol 1 was recovered and recycled.

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 1122-61-8, 4-Nitropyridine.

Reference:
Article; Giomi, Donatella; Alfini, Renzo; Brandi, Alberto; Tetrahedron; vol. 67; 1; (2011); p. 167 – 172;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 884494-69-3, 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 884494-69-3, name is 3-Fluoro-2-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 3-fluoro-2-methoxypyridine (20g, 157.48mmol), sodium acetate (25.74g, 314.0 mmol) inAcOH (6OmL) was added dropwise a solution of Br2 (20.32mL, 393.70mmol) in AcOH (40 mL) at 10Cand the RM stirred at RT for 16h.The RM was quenched into ice water (200mL) and then basified with 6N NaOH solution to pH 9 and filtered the solid. The solid was dissolved in Et2O (300mL), washed with brine, dried (Na2SO4), filtered, concentrated under reduced pressure to give 5-bromo-3-fluoro-2- methoxypyridine (20g, 61%) as white solid

According to the analysis of related databases, 884494-69-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GRUeNENTHAL GMBH; SCHUNK, Stefan; REICH, Melanie; JAKOB, Florian; DAMANN, Nils; HAURAND, Michael; KLESS, Achim; ROGERS, Marc; SUTTON, Kathy; WO2015/158427; (2015); A1;,
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. 1221171-70-5, name is 2-Chloro-6-(trifluoromethoxy)pyridine. A new synthetic method of this compound is introduced below., Recommanded Product: 1221171-70-5

Butyllithium (1.56 M in hexanes, 5.7 mL, 8.9 mmol, 1.1 equiv.) was added dropwise at 0 C to a solution of diisopropylamine (1.2 mL,8.9 mmol, 1.1 equiv.) in THF (15 mL). A solution of 2-chloro-6-(trifluoromethoxy)pyridine 2 (1.6 g, 8.1 mmol, 1 equiv.) in THF (5 mL) was added dropwise at-78 C, and the reaction mixture was stirred for 2 h at this temperature. Chlorotrimethylsilane (1.0 g, 1.13 mL,8.9 mmol, 1.1 equiv.) was then added dropwise and the mixture was allowed to reach 25 C before being neutralised with water (20 mL) andextracted with diethyl ether (3 ×10 mL). The combined organic layerswere dried over sodium sulphate and concentrated in vacuo. The crude product was distilled under reduced pressure to afford pure 2-chloro-6-(trifluoromethoxy)-5-(trimethylsilyl)pyridine (3). Colourless oil (1.5 g,68%), b.p.= 89-93 C (14 mbar); 1H NMR (CDCl3, 300 MHz, 25 C): delta7.78 (d, 1H, J =7.6 Hz, H-3), 7.22 (d, 1H, J =7.6 Hz, H-4), 0.34 (s,9H, SiMe3) ppm.

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, 1221171-70-5, 2-Chloro-6-(trifluoromethoxy)pyridine.

Reference:
Article; Landelle, Gregory; Schmitt, Etienne; Panossian, Armen; Vors, Jean-Pierre; Pazenok, Sergiy; Jeschke, Peter; Gutbrod, Oliver; Leroux, Frederic R.; Journal of Fluorine Chemistry; vol. 203; (2017); p. 155 – 165;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.73406-50-5, name is Ethyl 3-hydroxypicolinate, molecular formula is C8H9NO3, molecular weight is 167.162, as common compound, the synthetic route is as follows.Formula: C8H9NO3

3-Hydroxy-picolinic acid (15.6 g, 42.1 mmol), ethanol (360 mL), benzene (100 mL) and 98% sulfuric acid (6 mL) were heated under reflux for 40 h. After evaporation of the ethanol and benzene, the residue was dissolved in water, neutralized with sodium bicarbonate, and extracted with chloroform. The organic layer was dried (MgS04), filtered, and then the solvent was evaporated to give ethyl 3-hydroxy-picolinate as a brown oily residue (11.0 g).A mixture of ethyl 3-hydroxy-picolinate (11.0 g, 65.8 mmol), ethyl bromoacetate (12.1 g, 72.4 mmol) and anhydrous potassium carbonate (11.8 g, 85.5 mmol) in acetone (120 mL) was heated under reflux for 15 h. After cooling, the inorganic material separated by filtration. The filtrate was dissolved in chloroform, washed with water, then brine and dried (MgSO4), filtered, and the solvent was evaporated to give a brown oily residue. The residue was purified by flash chromatography using a gradient of ammoniated methanol in chloroform to give ethyl 2- (2-ethoxycarbonyl-3-pyridyloxy) acetate (13.7 g) as a yellow oil (13.7 g). Ethyl 2- (2-ethoxycarbonyl-3-pyridyloxy) acetate (13.6 g, 54.0 mmol) and sodium ethoxide (8. 08 g, 118.8 mmol) in toluene (200 mL) were heated under reflux for 18 h. After cooling, a precipitate was collected by filtration, dissolved in the minimum amount of hot water (about 300 mL), and acidified with acetic acid (6 mL). The resulting precipitate was filtered, and dried in vacuo to give ethyl 3-hydroxyfuro [3,2-b] pyridine-2-carboxylate as a solid (7.0 g). Ethyl 3-hydroxyfuro [3,2-b] pyridine-2-carboxylate (6.90 g, 25.8 mmol) was dissolved in 10% hydrochloric acid (50 mL), and heated under reflux for 3 h. Evaporation of the hydrochloric acid solution gave furo [3,2-b] pyridin-3 (2H)-one hydrochloride (9.0 g). A portion of the furo [3,2-b] pyridin-3 (2H) -one hydrochloride was converted to its free base by treatment with saturated sodium bicarbonate and extraction with chloroform in preparation for the following step. N, N-Diisopropylethylamine (1.08 g, 8.34 mmol) was added slowly to a solution of furo [3,2-b] pyridin-3 (2H) -one (1.40 g, 7.25 mmol) in dry dichloromethane (60 mL) under nitrogen at-10°r; C. Then trifluromethanesulfonic anhydride (2.45 g, 8.70 mmol) was added slowly. The mixture was warmed to RT, and stirred overnight. The reaction was quenched with water. The organic layer was washed with water and brine, dried (MgS04), and then the solvent was evaporated to give a brown oily residue, which was purified by flash chromatography using chloroform to give the sub-title compound (980 mg) as a light-brown oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73406-50-5, Ethyl 3-hydroxypicolinate, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/42538; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem