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. 115473-15-9, name is 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride. A new synthetic method of this compound is introduced below., 115473-15-9

Into a reaction flask equipped with a stirrer, a condenser, and a thermometer was charged intermediate II-113.16 g,This was dissolved in 15 ml of toluene, and 2.37 g of pyridine was added under stirring.1.91 g of 5,6,7,7a-tetrahydrothieno [3,2-c] pyridin-2 (4H) -one hydrochloride was added portionwise to the reaction system.The reaction was continued at 90 C for 2 h after completion of the dropwise addition.The reaction mixture was washed with 3 x 18 ml of water, the toluene layer was separated, dried over anhydrous sodium sulfate,Filtration and distillation of the toluene under reduced pressure gave 3.8 g of a colorless oily product (HPLC: 98.8%),Rf = 0.53 (single spot, developing solvent; v (petroleum ether): v (ethyl acetate) = 2: 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,115473-15-9, 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Tianjin Institute of Pharmaceutical Research; LIU, DENG KE; MU, SHUAI; LIU, YING; NIU, DUAN; TAN, CHU BING; ZHOU, ZHI XING; LIU, CHANG XIAO; (22 pag.)CN103896962; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 100-26-5 as follows., 100-26-5

10311] Thionyl chloride (2.2 mE) was added dropwise to MeOH (14 mE) while stirring on ice. 2,5-Pyridinedicarbox- ylic acid (1.0 g, 6.0 mmoles) was added and the reaction heated at reflux for 3 hr. The reaction was cooled and the solvent removed under reduced pressure. The resulting residue was dissolved in DCM (15 mE), afier which saturated Na2CO3 (15 mE) was added while stirring on ice. Theaqueous layer was extracted with DCM (3x 15 mE), and the combined organics were washed with saturated Na2CO3 (2×40 mE), dried over Na2SO4(s), and concentrated under reduced pressure to afford the title compound (915 mg, 78%) as a pale yellow solid. ?H NMR (500 MHz, CDC13) oe 9.32 (dd, J=0.5, 2.0 Hz, 1H), 8.47 (dd, J=2.0, 8.0 Hz, 1H), 8.23 (dd, J=0.5, 8.0 Hz, 1H), 4.06 (s, 3H), 4.01 (s, 3H); ?3C NMR (125 MHz, CDC13) oe 165.0, 164.9, 150.8, 150.8, 138.4, 128.6, 124.7, 53.3, 52.8; HRMS (ESI) mlz 196.0600 [calc?d for C9H,QNO4 (M+H) 196.0605].

The chemical industry reduces the impact on the environment during synthesis 100-26-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; WISCONSIN ALUMNI RESEARCH FOUNDATION; RAINES, Ronald T.; Vasta, James; (50 pag.)US2016/280701; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

571188-59-5, 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 571188-59-5 as follows.

To a 500 ml round bottom flask was added 16.8 g of compound 7 (50 mmol).18.4 g of compound 8 (60 mmol) was dissolved in 350 ml of toluene and refluxed. After the reaction was completed,The solvent was evaporated under reduced pressure and the residue was dissolved in methanol (300 ml).Adding dilute hydrochloric acid to room temperature reaction,After the reaction is completed, it is alkalized to pH>10 with dilute aqueous ammonia, extracted with ethyl acetate, and washed with saturated brine.Dried over anhydrous sodium sulfate and concentrated to give a white solid compound.The target product after recrystallization (1) 14 g, 65%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,571188-59-5, its application will become more common.

Reference:
Patent; Southwest University for Nationalities; Song Lei; (9 pag.)CN108623599; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 1003-68-5 as follows., 1003-68-5

To 144 5-methyl-1H-pyridin-2-one (2.0 g, 18 mmol), 96 1-iodo-4-(trifluoromethyl)benzene (5.9 g, 22 mmol), 12 copper(I) iodide (6.7 g, 3.6 mmol), 13 potassium phosphate (7.7 g, 37 mmol) and 145 N,N’-dimethylethylenediamine (0.70 g, 7.3 mmol) was added 126 1,4-dioxane (15 mL), and the mixture was stirred under a nitrogen atmosphere at 109C overnight. Insoluble material was filtered off through celite, the filtrate was poured into water and the mixture was extracted three times with ethyl acetate. The organic layer was dried over sodium sulfate. The desiccant was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate) to give the 146 title compound (4.2 g, 17 mmol, 91%). 1H NMR (400 MHz, DMSO-d6) delta7.90 (d, J = 8.0 Hz, 2H), 7.68 (d, J = 8.4, Hz, 2H), 7.52 (s, 1H) 7.41 (dd, J = 2.8, 9.6 Hz, 1H), 6.48 (d, J = 9.2 Hz, 1H) 2.05 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 1003-68-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; EA Pharma Co., Ltd.; KOBAYASHI, Kaori; SUZUKI, Tamotsu; OKUZUMI, Tatsuya; (110 pag.)EP3412664; (2018); A1;,
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.1124-64-7, name is 1-Butylpyridinium Chloride, molecular formula is C9H14ClN, molecular weight is 171.67, as common compound, the synthetic route is as follows.1124-64-7

1-butylpyridinium chloroaluminate was prepared by slowly mixing dried 1 -butylpyridinium chloride and anhydrous aluminum chloride (AlCl3) according to the following procedure. The 1-butylpyridinium chloride (prepared as described above) was dried under vacuum at 80 C. for 48 hours to get rid of residual water (1-butylpyridinium chloride is hydroscopic and readily absorbs water from exposure to air). Five hundred grams (2.91 mol.) of the dried 1-butylpyridinium chloride were transferred to a 2-Liter beaker in a nitrogen atmosphere in a glove box. Then, 777.4 gm (5.83 mol.) of anhydrous powdered AlCl3 (99.99% from Aldrich) were added in small portions (while stirring) to control the temperature of the highly exothermic reaction. Once all the AlCl3 was added, the resulting amber-looking liquid was left to gently stir overnight in the glove box. The liquid was then filtered to remove any un-dissolved AlCl3. The resulting acidic 1-butyl-pyridinium chloroaluminate was used as the catalyst for the alkylation of isopentane with ethylene.

Statistics shows that 1124-64-7 is playing an increasingly important role. we look forward to future research findings about 1-Butylpyridinium Chloride.

Reference:
Patent; Chevron U.S.A. Inc.; US2007/225538; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

16013-85-7, 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 16013-85-7, name is 2,6-Dichloro-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Reference Example 15 2,6-dibromo-3-nitropyridine 2,6-Dichloro-3-nitropyridine (5.0 g) was dissolved in 25% hydrogen bromide-acetic acid solution (50 mL), and the mixture was stirred at 80C for 6 hr. The mixture was returned to room temperature, concentrated under reduced pressure to a liquid amount of about 20 mL, neutralized using a 12N aqueous sodium hydroxide solution at 0C, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The yellow solid obtained as a residue was washed with a mixed solvent of diisopropyl ether and hexane to give the title compound as yellow crystals (yield 5.6 g, including impurity). 1H-NMR (CDCl3) delta: 7.65 (1H, d, J = 8.4 Hz), 8.03 (1H, d, J = 8.4 Hz).

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 16013-85-7, 2,6-Dichloro-3-nitropyridine.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1787991; (2007); 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. 19524-06-2, name is 4-Bromopyridine hydrochloride, the common compound, a new synthetic route is introduced below. 19524-06-2

A mixture of 4-fluorobenzeneboronic acid (38.7 g, 276 mmol), 4-bromopyridine hydrochloride (48.9 g, 250 mmol), [1,4-butanediylbis(diphenylphosphine-kappaP)]dichloropalladium (Organometallics 1998, 17, 661; 1.52 g, 2.5 mmol), 1,2-dimethoxyethane (500 mL) and sodium carbonate solution (2M, 440 mL) was degassed with bubbling nitrogen and stirred at 8020 C. for 24 hours. The mixture was cooled and extracted with ethyl acetate. The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure to give the crude title compound as a brown solid (50.87 g) which was used without further purification. 1H NMR (360 MHz, CDCl3) delta8.65 (2H, m), 7.61 (2H, m), 7.49 (2H, dd, J 1.6, 4.6 Hz), and 7.09 (2H, m).

Statistics shows that 19524-06-2 is playing an increasingly important role. we look forward to future research findings about 4-Bromopyridine hydrochloride.

Reference:
Patent; Pineiro, Jose Luis Castro; Dinnell, Kevin; Elliott, Jason Matthew; Hollingworth, Gregory John; Shaw, Duncan Edward; Swain, Christopher John; Yang, Lihu; US2003/225059; (2003); A1;,
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. 13534-99-1, name is 2-Amino-3-bromopyridine, molecular formula is C5H5BrN2, 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. 13534-99-1

Step A: 3-Phenylpyridin-2-amineTo a deoxygenated solution of 3-bromopyridin-2-amine (5.00 g, 28.9 mmol), phenylboronic acid (4.23 g, 34.7 mmol) and sodium carbonate (9.2 g, 87 mmol) in 1,4-dioxane (60 mL) and water (30 mL) was added PdCl2(PPh3)2 (1.01 g, 1.44 mmol). The resulting mixture was heated at reflux for 4 h, then cooled, filtered, and concentrated. The residue was partitioned between brine (50 mL) and ethyl acetate (30 mL x 3). The combined organic layers were washed with brine, dried over Na2S04, and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate in petroleum ether: 20-50%) to give the title compound. XH NMR (400 MHz, CDC13) delta 8.09 (d, J= 3.5 Hz, 1H), 7.51-7.43 (m, 4H), 7.41-7.35 (m, 2H), 6.76 (dd, J= 7.0, 5.1 Hz, 1H), 4.61 (br s, 2H).

The chemical industry reduces the impact on the environment during synthesis 13534-99-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; MITCHELL, Helen; FRALEY, Mark, E.; COOKE, Andrew, J.; CHEN, Yi-Heng; STUMP, Craig, A.; ZHANG, Xu-Fang; MCCOMAS, Casey, C.; SCHIRRIPA, Kathy; MCWHERTER, Melody; MERCER, Swati, P.; BABAOGLU, Kerim; MENG, Dongfang; WU, Jane; LIU, Ping; WOOD, Harold, B.; BAO, Jianming; LI, Chun Sing; MAO, Qinghua; QI, Zhiqi; (263 pag.)WO2015/148344; (2015); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

504-29-0, 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. 504-29-0, name is Pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

S1. Dichloromethane (900 g) was added to a 2 L three-neck bottle at room temperature. 2-Aminopyridine (135 g, 1.0 eq), triethylamine (174 g, 1.2 eq), Cool down to 10-20 C, add pivaloyl chloride (189 g, 1.1 eq), After the addition is completed, the system is warmed to 20-25 C, and the reaction is 2-3 h; After the reaction was completed, water was added to the reaction system, and after stirring for 0.5 h, the organic phase was separated. The aqueous phase was extracted with dichloromethane (500 g). Add petroleum ether (800g) directly at 0 C, stir for 2 h, suction filtration, 2-Pentylaminopyridine was obtained in a yield of 83%.

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, 504-29-0, Pyridin-2-amine.

Reference:
Patent; Aisite (Chengdu) Bio-pharmaceutical Co., Ltd.; Luo Jianye; Li Hongqiang; Guo Peng; (10 pag.)CN108675954; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

100-48-1, 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. 100-48-1, name is Isonicotinonitrile. A new synthetic method of this compound is introduced below.

Reference Example 2: Synthesis of 4-(5-amino-1,2,4-oxadiazol-3-yl)pyridine. 17.1 g of 4-cyanopyridine, 70 ml of water, 11.4 g of hydroxylamine hydrochloride and 8.7 g of Na2CO3 were stirred in an autoclave for 8 hours with heating at 70C and, after cooling, the resulting reaction mixture was mixed with 60 ml of water, heated again and then spontaneously cooled to obtain 20.8 g of isonicotinamidoxime.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100-48-1, Isonicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; KATAYAMA SEIYAKUSYO CO. Ltd.; Ajinomoto Co., Inc.; EP641797; (1995); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem