Category: pyridine-derivatives

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. 73583-37-6, name is 4-Bromo-2-chloropyridine. A new synthetic method of this compound is introduced below., SDS of cas: 73583-37-6

The compound obtained in Step 1 670 mg (2.03 mmol) to 10 ml of 1,4-dioxane was dissolved in then PdCl2 (dppf) 2.CH2Cl2 163 mg (0.20 mmol) and 4-bromo-2-chloropyridine 1.16 g (6.09 mmol), 2M- sodium carbonate (Na2CO3) aqueous solution was added to 3.05 ml (6.09 mmol) was stirred under reflux at 110 for 4 hours. Celite (celite), filtered and concentrated under reduced pressure the filtrate was purified by silica gel column chromatography (dichloromethane: methanol = 3: 1, v / v) 380 to yield a target compound as a yellow solid in a yield of 60% mg (1.20 gained mmol)

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, 73583-37-6, 4-Bromo-2-chloropyridine.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; LEE, KYU YANG; IM, JAE CHO; LEE, BYUNG HO; OH, KWANG SEOK; KIM, JEONG YEONG; OH, SEUNG AE; LEE, JEONG HYUN; (38 pag.)KR2015/117319; (2015); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 5435-54-1, 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. 5435-54-1, name is 3-Nitropyridin-4-ol. A new synthetic method of this compound is introduced below.

a) 4-Chloro-3-nitropyridine Phosphorus oxychloride (25 ml, 0.27 mol) was added to 4-hydroxy-3-nitropyridine (7.0 g, 50.0 mmol), followed by reaction at 80 to 90 C. for 1.5 hours. Phosphorus oxychloride was removed by distillation. About 100 g of ice was added to the residue, and 28% aqueous ammonia was added dropwise thereto to adjust the pH to 7. Then, 100 ml of water was added thereto, and the aqueous mixture was extracted three times with 200 ml of dichloromethane. The resulting dichloromethane layer was dried, and then dichloromethane was removed by distillation under reduced pressure to obtain 7.75 g of a yellow liquid (yield: 97.8%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5435-54-1, 3-Nitropyridin-4-ol, and friends who are interested can also refer to it.

Reference:
Patent; The Green Cross Corporation; US5262415; (1993); A;,
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. 86873-60-1, name is 5-Chloro-2-picolinic acid. This compound has unique chemical properties. The synthetic route is as follows. Safety of 5-Chloro-2-picolinic acid

B. 5-Chloropyridine-2-carbonyl chloride To a dry 250 mL round-bottom flask equipped with magnetic stirrer and reflux condenser was charged 5 g of 5-chloropyridine-2-carboxylic acid (0.0317 mol), 100 mL methylene chloride, and 5 drops of DMF as a catalyst. Some of the solid did not dissolve. Thionyl chloride (10 mL; 0.137 mol) was added in one portion, and the reaction was refluxed for a total of 7 hours. After cooling, the reaction was stripped to dryness and 5.1 g of a white solid was isolated. The NMR data is as follows: 300 MHz 1H NMR (CDCl3, TMS=0 ppm) 1.25 (t, 3H); 1.48 (s, 18H); 2.05 (d, 2H); 3.65 (t, 1H); 4.15 (q, 2H). The sample was stored in the refrigerator and had 59% isolated yield. The sample was used without additional purification and had 91% isolated yield.

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, 86873-60-1, 5-Chloro-2-picolinic acid.

Reference:
Patent; DOW AGROSCIENCES LLC; US2009/253708; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1020253-15-9, 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.1020253-15-9, name is 4-Bromo-2-chloro-5-methoxypyridine, molecular formula is C6H5BrClNO, molecular weight is 222.47, as common compound, the synthetic route is as follows.

Step 105.2: 4-Bromo-5-methoxy-1-methyl-1 H-pyridin-2-one A solution of 4-bromo-2-chloro-5-methoxypyridine (1 g, 4.5 mmol) in dimethyl sulfate (1.9 mL, 19.5 mmol) was stirred at 120C for 16 h in a sealed tube. After cooling, acetonitrile and a saturated aqueous NaHC03 solution were added and the mixture was stirred at rt over week-end. DCM was added and extracted. The organic layer was dried (Na2S04), filtered and concentrated to give the title compound. tR: 0.57 min (LC-MS 2); ESI-MS: 218.0/220.0 [M+H]+ (LC-MS 2).

The chemical industry reduces the impact on the environment during synthesis 1020253-15-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; GUAGNANO, Vito; HOLZER, Philipp; KALLEN, Joerg; LIAO, Lv; MAH, Robert; MAO, Liang; MASUYA, Keiichi; SCHLAPBACH, Achim; STUTZ, Stefan; VAUPEL, Andrea; WO2013/111105; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 131084-55-4, name is 5-Chloro-1H-pyrrolo[2,3-c]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C7H5ClN2

5-Chloro-lH-pyrrolo[2,3-c]pyridine (400.0 mg, 2.614 mmol, 1.0 eq) was dissolved in DMF (20.0 mL). After cooling to 0 C, NIS (882 mg, 3.922 mmol, 1.5 eq) was added and the resulting mixture was stirred at rt for 18 h, then concentrated in vacuo. The resulting residue was purified by column chromatography to provide 5-chloro-3-iodo-lH- pyrrolo[2,3-c]pyridine (725 mg, ca 100%).

With the rapid development of chemical substances, we look forward to future research findings about 131084-55-4.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (346 pag.)WO2018/11628; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 89-00-9 , The common heterocyclic compound, 89-00-9, name is Pyridine-2,3-dicarboxylic acid, molecular formula is C7H5NO4, 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.

Pyridine-2,3-dicarboxylic acid (8.40 g, 50.30 mmol, 1 eq) was suspended in acetic anhydride (11.0 mL, 116.50 mmol, 2.3 eq) and the mixture was heated at 120 C, distilling 9.5 mL of acetic acid. After cooling at 100 C the acetamide (6.70 g, 113.60 mmol, 2.2 eq) was added portionwise in 5 min. The reaction was then heated at reflux for 2.5 h. After cooling at room temperature, the precipitate was filtered off and washed with water (2 * 12 mL) to give the desired product as grey solid after crystallization with EtOH/H2O 95:5 (3.46 g, 47%). Mp. 230-231 C. 1H NMR (300 MHz, DMSO-d6) delta 11.63 (br s, NH), 8.93 (d, J = 4.9 Hz, 1-H), 8.22 (d, J = 7.7 Hz, 1-H), 7.74 (dd, J = 7.6/4.9 Hz, 1-H). IR (KBr) 3483, 3189, 3100, 1735, 1704 cm-1.

The synthetic route of 89-00-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Galli, Ubaldina; Mesenzani, Ornella; Coppo, Camilla; Sorba, Giovanni; Canonico, Pier Luigi; Tron, Gian Cesare; Genazzani, Armando A.; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 58 – 66,9;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 101990-69-6, Adding some certain compound to certain chemical reactions, such as: 101990-69-6, name is 2,6-Dichloropyridine-4-methanol,molecular formula is C6H5Cl2NO, 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 101990-69-6.

a) 4-(tert-Butyl-dimethyl-silanyloxymethyl)-2,6-dichloro-pyridine; A solution of 2,6-dichloropyridine-4-methanol (150 mg, 0.84 mmol), tert-butyl-chloro-dimethyl-silane (152 mg, 1.01 mmol) and imidazol (143 mg, 2.01 mmol) in 1 mL of N,N-dimethylformamide was stirred overnight at. The reaction mixture was concentrated in the rotatory evaporator, water was added and the slurry extracted with ethyl acetate. Chromatography on amino-modified silica gel (Merck HPTLC Silica Gel 60 NH2F254S) using heptane/ethylacetate (gradient 0 to 50% ethyl acetate) gave the pure title compound as a colorless solid (160 mg, 65%). MS ISP (m/e): 292.1 & 294.0 (100 & 97) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): delta (ppm)=7.21 (s, 2H), 4.70 (s, 2H), 0.95 (s, 9H), 0.12 (6H).

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. 101990-69-6, 2,6-Dichloropyridine-4-methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Baumann, Karlheinz; Flohr, Alexander; Goetschi, Erwin; Jacobsen, Helmut; Jolidon, Synese; Luebbers, Thomas; US2009/215759; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 769-28-8, Adding some certain compound to certain chemical reactions, such as: 769-28-8, name is 4,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile,molecular formula is C8H8N2O, 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 769-28-8.

Example 6 3-(5-_ELhLI-2,4-dimgLhyl-6-oxo-1,6-dihydroMidin-3-yl)benzonitrile Step 1: 2-Chloro-3-cyano-4,6-dimethylpyridine: A stirred mixture of 3-cyano-4,6-dimethyl- 2-hydroxypyridine (4.35 g, 29.39 mmol) and phosphorous pentachloride (6.92 g, 33.21 mmol) is heated to 120C. The reaction mixture becomes clear and is stirred for an additional 1 hr. It is then poured onto ice/water (250 mL) and allowed to stand for 30 min. The solution is neutralized with sodium bicarbonate (pH 6) and extracted with dichloromethane (400 mL). The separated organic layer is dried, filtered and concentrated to yield 2-chloro-3-cyano-4,6- dimethylpyridine (4.60 g, 94% yield) as a tan solid containing ca 15% impurity. LC/MS: MS m/e = 167/169 (M + H) ; RT 2.98 min; NMR (CDCl3, 8 ppm) 7.08 (1H, s), 2.57 (3H, s), 2.55 (3H, s).

According to the analysis of related databases, 769-28-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AVENTIS PHARMACEUTICALS INC.; WO2005/97750; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 33252-30-1, name is 2-Chloroisonicotinonitrile, the common compound, a new synthetic route is introduced below. Quality Control of 2-Chloroisonicotinonitrile

General procedure: Aromatic or aliphatic nitriles (2 mmol) were dissolved in 5 ml of [bmim]HSO4 and the reaction mixture was heated at 60-65 C for 1-3 h. The progress of reaction was monitored by TLC. After completion of reaction, as checked by TLC, the reaction mixture was poured into water containing crushed ice. The product was precipitated out, filtered and dried. The yield of the final product was high (>90%) in all cases. All final products obtained were found sufficiently pure so it didn?t need further purification.The filtrate was concentrated under vacuum, washed with diethylether twice and concentrated under high vacuum. After proper drying under reduced pressure, approximately 95% ionic liquid was recovered from the reaction and compared with the original ionic liquid to check its authenticity. The efficiency of recovered ionic liquid in conversion of nitriles to acids was found unchanged in comparison to the original one and we reused it up to 5-6 cycles without any significant loss of its activity.

The synthetic route of 33252-30-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kumar, Satyanand; Dixit, Sandeep Kumar; Awasthi, Satish Kumar; Tetrahedron Letters; vol. 55; 28; (2014); p. 3802 – 3804;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 73998-95-5, name is (4,6-Dichloropyridin-3-yl)methanol, molecular formula is C6H5Cl2NO, 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. Quality Control of (4,6-Dichloropyridin-3-yl)methanol

Part II — Synthesis of 4,6-dichloropyridine-3-carbaldehyde [0231] (4,6-Dichloropyridin-3-yl)methanol (4.9 g, 28 mmol) was dissolved in CHC13 (100 mL). Mn02 (24 g, 280 mmol) was then added and the reaction mixture was stirred at 75 C for 12 hours. Next, the reaction was cooled to room temperature, filtered through Celite, and concentrated to give 4,6-dichloropyridine-3-carbaldehyde. Yield 2.9 g (90%>). LCMS (ESI): calc. C6H3C12N0 = 175; obs. M+H = low ionization.

With the rapid development of chemical substances, we look forward to future research findings about 73998-95-5.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LYCERA CORPORATION; AICHER, Thomas; BARR, Kenneth; LAPOINTE, Blair; SIMOV, Vladimir; STEIN, Karin; THOMAS, William; TOOGOOD, Peter; VAN HUIS, Chad; WHITE, Catherine; WO2013/169704; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem