Category: 74115-12-1

Reference of 74115-12-1, 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.74115-12-1, name is 5-Chloro-3-hydroxypyridine, molecular formula is C5H4ClNO, molecular weight is 129.5444, as common compound, the synthetic route is as follows.

With ice cooling, 30 g of 5-chloropyridin-3-ol (232 mmol, 1 equivalent) were dissolved in 228 ml of concentrated sulfuric acid, and 24 ml of concentrated nitric acid were added slowly at 0 C. The reaction was warmed to RT and stirred overnight. The mixture was stirred into an ice/water mixture and stirred for 30 min. The solid was filtered off, washed with cold water and air-dried. This gave 33 g (82% of theory) of the title compound which was used without further purification for the next reaction. LC-MS (Method 1): Rt=0.60 min MS (ESneg): m/z=172.9/174.9 (M-H)- 1H-NMR (400 Mhz, DMSO-d6): delta=7.71 (d, 1H); 8.10 (d, 1H); 12.14 (br. 1H).

The chemical industry reduces the impact on the environment during synthesis 74115-12-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; VAKALOPOULOS, Alexandros; BROCKSCHNIEDER, Damian; WUNDER, Frank; STASCH, Johannes-Peter; MARQUARDT, Tobias; DIETZ, Lisa; LI, Volkhart Min-Jian; (50 pag.)US2017/304278; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 74115-12-1, 5-Chloro-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, Application In Synthesis of 5-Chloro-3-hydroxypyridine, blongs to pyridine-derivatives compound. Application In Synthesis of 5-Chloro-3-hydroxypyridine

Example 15A 5-Chloro-2-nitropyridin-3-ol With ice cooling, 30 g of 5-chloropyridin-3-ol (232 mmol, 1 equivalent) were dissolved in 228 ml of concentrated sulphuric acid, and, at 0 C., 24 ml of concentrated nitric acid were added slowly. The reaction was warmed to RT and stirred overnight. The mixture was stirred into an ice/water mixture and stirred for another 30 min. The solid was filtered off, washed with cold water and air-dried. This gave 33 g (82% of theory) of the title compound, which were used without further purification for the next reaction. LC-MS (Method 1): Rt=0.60 min MS (ESneg): m/z=172.9/174.9 (M-H)- 1H NMR (400 MHz, DMSO-d6): delta=7.71 (d, 1H); 8.10 (d, 1H); 12.14 (br. 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,74115-12-1, 5-Chloro-3-hydroxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; VAKALOPOULOS, Alexandros; HARTUNG, Ingo; FOLLMANN, Markus; JAUTELAT, Rolf; STRAUB, Alexander; HAssFELD, Jorma; LINDNER, Niels; SCHNEIDER, Dirk; WUNDER, Frank; STASCH, Johannes-Peter; REDLICH, Gorden; LI, Volkhart Min-Jian; BECKER-PELSTER, Eva Maria; KNORR, Andreas; US2014/128386; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 74115-12-1, 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. 74115-12-1, name is 5-Chloro-3-hydroxypyridine, molecular formula is C5H4ClNO, 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.

7-((Difluoromethyl)sulfonyl)-4- fluoro-2,3-dihydrospiro[indene-l ,2′-[l,3]dioxolane] (3.0 g, 9.7 mmol) was combined with 5- chloropyridin-3-ol (1.89 g, 14.6 mmol) and sodium bicarbonate (2.45 g, 29.2 mmol) then the solids were suspended in N-methylpyrrolidinone (28.5 mL). The mixture was heated to 90 C for 14 hours then stirred at ambient temperature for 34 hours. The reaction mixture was diluted with ethyl acetate and water and the layers were separated. The aqueous was washed with ethyl acetate and the combined organic layers were washed five times with water, saturated NaCl, dried over Na2S04 and concentrated in vacuo to a cream-colored solid (4.36 g). LCMS ESI (+) m z (Mu+Eta) 418, 420.

According to the analysis of related databases, 74115-12-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PELOTON THERAPEUTICS, INC.; DIXON, Darryl, David; GRINA, Jonas; JOSEY, John, A.; RIZZI, James, P.; SCHLACHTER, Stephen, T.; WALLACE, Eli, M.; WANG, Bin; WEHN, Paul; XU, Rui; YANG, Hanbiao; WO2015/35223; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 74115-12-1 , The common heterocyclic compound, 74115-12-1, name is 5-Chloro-3-hydroxypyridine, molecular formula is C5H4ClNO, 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.

Example 12 Preparation of Compound 7 (0241) (0242) To a 0 C. solution of 5-chloro-3-hydroxypyridine (3.00 g, 23.16 mmol) in tetrahydrofuran (90 mL) was added lithium tert-butoxide (1.0 M in THF, 23.16 ml, 23.16 mmol) dropwise, so as to maintain the internal reaction temperature below 10 C. (0243) In a separate flask, compound 12a (10.0 g, 22.1 mmol) was dissolved in tetrahydrofuran (50.0 mL). This solution was added dropwise to the lithium phenoxide solution over 2 min below 10 C. The cooling bath was then removed. This solution was then added dropwise to the lithium phenoxide solution over a 5 minute period while maintaining the internal reaction temperature below 10 C. The mixture was aged at 0-10 C. for 2 hours, then 0.5M aqueous citric acid (150 mL) and MTBE (100 mL) were added. The organics were dried over MgSO4, filtered, concentrated in vacuo, and purified using silica gel chromatography (0:100 to 70:30 EtOAc:Hexanes) to provide compound 7 (8.1 g, 22.4 mmol, 92% yield). 1H-NMR delta (ppm)(DMSO-d6): 1.11 (6H, dd, J=6.3, 3.3 Hz), 1.20 (3H, d, J=7.1 Hz), 3.89-3.97 (1H, m), 4.79-4.84 (1H, m), 6.71 (1H, dd, J=14.2, 10.1 Hz), 7.24 (1H, t, J=7.4 Hz), 7.29 (2H, d, J=8.1 Hz), 7.42 (2H, t, 7.8 Hz), 7.86 (1H, d, J=2.0 Hz), 8.47 (1H, s), 8.53 (1H, d, J=2.1 Hz).

The synthetic route of 74115-12-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EDWARDS, John Simon; MULLENS, Peter Richard; CLEATOR, Edward; MAGUIRE, Courtney K.; SCOTT, Jeremy Peter; ZHONG, Yong; FREY, Lisa F.; DORMER, Peter G.; KLAPARS, Artis; ASHLEY, Eric; QIAN, Pu; MERCK SHARP & DOHME CORP.; MERCK SHARP & DOHME LIMITED; Edwards, John; Mullens, Peter Richard; Cleator, Ed; Simmons, Bryon L.; Maguire, Courtney K.; Scott, Jeremy Peter; Yasuda, Nobuyoshi; Zhong, Yong-Li; Frey, Lisa F.; Dormer, Peter G.; Brunskill, Andrew; Klapars, Artis; Qian, Puneet; Zhang, Yi; Wan, Baoqiang; (23 pag.)US2017/275327; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 74115-12-1 , The common heterocyclic compound, 74115-12-1, name is 5-Chloro-3-hydroxypyridine, molecular formula is C5H4ClNO, 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.

EXAMPLE 14; Preparation of 3-chloro-N-[(lS)-1-(4-chlorophenyl) ethyl]-5-(methoxymethoxy)-4-pyridine- carboxamide (Compound 179); Step A: Preparation of 3-chloro-5- (methoxymethoxy) pyridine; To a solution of 5-chloro-3-hydroxypyridine (Aldrich, 5 g, 39 mmol) in acetonitrile (60 mL) was added chloromethyl methyl ether (3.11 g, 39 mmol) followed by potassium carbonate (10.78 g). The mixture was heated at 60 C for 18 h and then diluted with water (100 mL). The aqueous layer was extracted with ethyl acetate (4 x 100 mL). The combined organic layers were dried (MgSO4), and the solvent was evaporated under reduced pressure to leave the title compound as a yellow oil (5.5 g). 1H NMR (CDC13) 8 3.49 (s, 3H), 5.30 (s, 2H), 7.42 (s, 1H), 8.26 (s, 1H), 8. 31 (s, 1H)

The synthetic route of 74115-12-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E.I. DUPONT DE NEMOURS AND COMPANY; WO2005/70889; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 74115-12-1, 5-Chloro-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, 74115-12-1, blongs to pyridine-derivatives compound. COA of Formula: C5H4ClNO

General procedure: A 4-halonitrobenzene (1.0 equiv), a hydroxyarene, and Cs2CO3 (1.1 equiv) were combined in DMF and the resulting heterogeneous mixture was stirred vigorously at 25-70 C until all 4-halonitrobenzene was consumed (2-24 h). The reaction mixture was diluted with H2O and was adjusted to pH 5 with 2 N HCl (aq). The solution was extracted three times with EtOAc, and the organic layers were combined, washed once with brine solution, dried over MgSO4, filtered and concentrated in vacuo to furnish the desired diaryl ether that was used directly without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,74115-12-1, its application will become more common.

Reference:
Article; Taygerly, Joshua P.; McGee, Lawrence R.; Rubenstein, Steven M.; Houze, Jonathan B.; Cushing, Timothy D.; Li, Yang; Motani, Alykhan; Chen, Jin-Long; Frankmoelle, Walter; Ye, Guosen; Learned, Marc R.; Jaen, Juan; Miao, Shichang; Timmermans, Pieter B.; Thoolen, Martin; Kearney, Patrick; Flygare, John; Beckmann, Holger; Weiszmann, Jennifer; Lindstrom, Michelle; Walker, Nigel; Liu, Jinsong; Biermann, Donna; Wang, Zhulun; Hagiwara, Atsushi; Iida, Tetsuya; Aramaki, Hisateru; Kitao, Yuki; Shinkai, Hisashi; Furukawa, Noboru; Nishiu, Jun; Nakamura, Motonao; Bioorganic and Medicinal Chemistry; vol. 21; 4; (2013); p. 979 – 992;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 74115-12-1, 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 74115-12-1, name is 5-Chloro-3-hydroxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

5-chloropyridin-3-ol(2.00 g, 15.4 mmol) was dissolved in concentrated H2SO4(15 mL) at 5 C. Concentrated nitric acid (1.0 mL) was then added. The reactionwas allowed to warm to room temperature over 3 hrs. The reaction solution waspoured onto ice water (25 mL). The resultant precipitate was filtered, washedwith water and dried overnight at 40 C in vacuo to afford was obtained as ayellow powder, (1.80g, 67%); H NMR (400 MHz, CDCI3) delta7.68 (d, 1H), 8.15 (d, 1H), 10.29 (s, 1H).

According to the analysis of related databases, 74115-12-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACTIVE BIOTECH AB; FRITZSON, Ingela; LIBERG, David; EAST, Stephen; MACKINNON, Colin; PREVOST, Natacha; WO2014/184234; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 74115-12-1, 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.74115-12-1, name is 5-Chloro-3-hydroxypyridine, molecular formula is C5H4ClNO, molecular weight is 129.5444, as common compound, the synthetic route is as follows.

To a solution of 5-chloropyridin-3-ol (6f) (1.30 g, 10.0 mmol) in THF (50 mL) was added Et3N (1.21 g, 12.0 mmol) and 1,1,1-trifluoro-N-phenyl-N-[(trifluoromethyl)sulfonyl]methanesulfonamide (3.93 g, 11.0 mmol) at room temperature. After stirring for 20 min, the solvent was removed under reduced pressure. The residue was partitioned between EtOAc and 1 mol/L HCl. The separated aqueous layer was extracted with EtOAc again. The combined extract was washed with brine, dried over anhydrous MgSO4, filtered, and then concentrated in vacuo. The residue was purified by silica gel column chromatography (n-hexane/EtOAc = 99/1-19/1) to afford compound 6a (1.73 g, 66%) as a colorless oil: 1H-NMR (CDCl3) d 7.69 (1H, t, J = 2.3 Hz), 8.52 (1H, d, J = 2.3 Hz), 8.64 (1H, d, J = 1.9 Hz).

Statistics shows that 74115-12-1 is playing an increasingly important role. we look forward to future research findings about 5-Chloro-3-hydroxypyridine.

Reference:
Article; Nishida, Haruyuki; Fujimori, Ikuo; Arikawa, Yasuyoshi; Hirase, Keizo; Ono, Koji; Nakai, Kazuo; Inatomi, Nobuhiro; Hori, Yasunobu; Matsukawa, Jun; Fujioka, Yasushi; Imanishi, Akio; Fukui, Hideo; Itoh, Fumio; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3447 – 3460;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 74115-12-1 ,Some common heterocyclic compound, 74115-12-1, molecular formula is C5H4ClNO, 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.

33b. 3-Chloro-2-(4-nitrophenylazo)-5-hydroxypyridine To a solution of 5-chloro-3-pyridinol (20.0 g, 0.154 mol, Aldrich) and KOH (13.0 g, 0.232 mol) in 300 mL of water at 0 C. was added p-nitrobenzenediazonium tetrafluoroborate (36.6 g, 0.154 mol, Aldrich). After 1 hour, 50 mL of glacial acetic acid was added, and the bright red precipitate was filtered and air-dried. Chromatography (silica gel; CH2 Cl2 /MeOH, 95:5-90:10) afforded the title compound as a bright red solid (28.8 g, 67%): 1 H NMR (DMSO-d6, 300 MHz) delta 7.14 (d, J=2.4 Hz, 1H), 7.89 (d, J=2.4 Hz, 1H), 8.00 (m, 2H), 8.39 (m, 2H); MS (CI/NH3) m/z: 279, 281 (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,74115-12-1, its application will become more common.

Reference:
Patent; Abbott Laboratories; US6133253; (2000); A;,
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. 74115-12-1, name is 5-Chloro-3-hydroxypyridine. A new synthetic method of this compound is introduced below., HPLC of Formula: C5H4ClNO

EXAMPLE 3 Synthesis of 5-Chloro-3-pyridinyl trifluoromethanesulfonate Trifluoromethanesulfonic anhydride (5.0 mL, 30 mmol) was dissolved in CH2Cl2 (100 mL), and cooled to 0 C. 5-Chloro-3-pyridinol (3.10 g, 23.9 mmol), and triethylamine (6.5 mL, 47 mmol) were dissolved in CH2Cl2 (50 mL), and the resulting solution was added to the cold trifluoromethanesulfonic anhydride solution dropwise via cannula. The resulting dark brownish-red solution was stirred at 0 C. for 5 minutes, and then the ice bath was removed and the reaction mixture was allowed to warm to ambient temperature. After stirring for 16 h at ambient temperature the reaction was quenched by pouring into water and basified by addition of saturated aqueous sodium carbonate. The basic aqueous phase was extracted with CH2Cl2 (2*50 mL), the combined organics dried over Na2SO4, filtered and concentrated in vacuo. The resulting black viscous oil was filtered through a plug of silica gel and fractions were collected while eluding with 1:1 hexane:ethyl acetate. Fractions containing the desired product were combined, concentrated in vacuo, and further purified by column chromatography eluding with 15:1 then 10:1 hexane:ethyl acetate to afford 5-chloro-3-pyridinyl trifluoromethanesulfonate (3.68 g, 59% yield) as a golden liquid. 1H NMR (CDCl3, 300 MHz) Delta8.65 (d, J=2 Hz, 1H), 8.52 (d, J=2 Hz, 1H), 7.70 (t, J=3 Hz, 1H). MS (ESI) 261 (M+, 35Cl), 263 (M+, 37Cl).

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, 74115-12-1, 5-Chloro-3-hydroxypyridine.

Reference:
Patent; Cosford, Nicholas D.; Roppe, Jeffrey R.; Tehrani, Lida R.; Smith, Nicholas D.; Stearns, Brian; Huang, Dehua; Wang, Bowei; US2005/43307; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem