Category: pyridine-derivatives

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. 868551-30-8, name is Methyl 4-methyl-5-nitropicolinate, the common compound, a new synthetic route is introduced below. HPLC of Formula: C8H8N2O4

Methyl 4-[(1E)-2-(dimethylamino)ethenyl]-5-nitro-2-pyridinecarboxylate (0628) (0629) 86.4 g (0.73 mmol) of 18 N,N-dimethylformamide O,O-dimethyl acetal were added to a solution of 65 g (0.33 mol) of 19 methyl 5-methyl-6-nitro-3-pyridinecarboxylate (Y. Morisawa et al., J. Med. Chem. 21, 194-199, 1978) in 415 ml of 20 N,N-dimethylformamide. The reaction mixture was then stirred at 90 C. for 6 hours. The solvent was then removed under reduced pressure and the residue that remained was purified by column chromatography. This gave 56 g (yield 66.7% of theory) of 21 methyl 4-[(1E)-2-(dimethylamino)ethenyl]-5mitro-2-pyridinecarboxylate.

The synthetic route of 868551-30-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer CropScience Aktiengesellschaft; JESCHKE, Peter; ARLT, Alexander; CEREZO-GALVEZ, Silvia; VOERSTE, Arnd; FUESSLEIN, Martin; FISCHER, Reiner; BRETSCHNEIDER, Thomas; ILG, Kerstin; MALSAM, Olga; LOESEL, Peter; GOERGENS, Ulrich; (74 pag.)US2017/325458; (2017); A1;,
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. 863878-22-2, name is 6-Chloro-4-methyl-3-nitropyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H6ClN3O2

2-Amino-6-chloro-4-methyl-3-nitropiridine (1.2 g, 6.40 mmol) synthesized according to the method described in WO98/02442 was dissolved in ethanol (65 mL), and tin(II) chloride dihydrate (4.33 g, 19.2 mmol) was added, followed by stirring at 75C for 2 hours. The reaction mixture was diluted with ethyl acetate and was added with 3 mol/L aqueous sodium hydroxide solution. The unsoluble material was filtered out through Celite, and washed with ethyl acetate. The filtrate was sequentially washed with water, saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Next, polyphosphoric acid (15.3 g) and acetic acid (1.72 mL, 30.0 mmol) was added to the residue, and was stirred for 80C for 3 hours. The reaction mixture was moved to ice water and sodium carbonate (11.4 g, 0.108 mol) was added in a little portion while stirring. Then, 28% aqueous ammonia solution was added to the residue to control the pH to 9 and the mixture was stirred for 1 hour. Precipitated crude crystals were collected by filtration, and werewashed with water, and the obtained crystals were dried in vacuo at 40C overnight to obtain Compound P38 (395 mg, 34%). ESI-MS: m/z 182 [M + H]+ 1H NMR (DMSO-d6)delta(ppm): 2.49 (s, 3H), 3.33 (s, 3H), 7.07 (s, 1H), 12.74 (brs, 0.5H), 12.76 (brs, 0.5H).

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, 863878-22-2, 6-Chloro-4-methyl-3-nitropyridin-2-amine.

Reference:
Patent; KYOWA HAKKO KOGYO CO., LTD.; EP1724271; (2006); 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. 179687-79-7, name is 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine, the common compound, a new synthetic route is introduced below. Formula: C12H9ClN2O3

A mixture of 2-((2-chloro-4-nitrophenoxy)methyl)pyridine (26.5 g, 0.10 mol, 1.00 equiv), iron powder (25.2 g, 0.43 mol, 4.28 equiv) and ammonium chloride (72.24 g, 1.35 mol, 13.5 equiv) in ethanol (600 ml) was stirred mechanically under refluxed for 2 hours. The reaction was allowed to cool down; the mixture of the reaction was filtered and the filtrate was taken to dryness in vacuum. The resulted solid was dissolved in methylene chloride (500 ml) and filtered. Removal of the solvent from the filtrate in vacuum gave 15.3 g of the product. MS (ESI) m/z: 235 (M+l).

The synthetic route of 179687-79-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDOLUTION LIMITED; ZHANG, Dawei; WO2010/151710; (2010); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 62734-08-1, 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.62734-08-1, name is 2-(Chloromethyl)-4-methoxypyridine hydrochloride, molecular formula is C7H9Cl2NO, molecular weight is 194.06, as common compound, the synthetic route is as follows.

Example 11; N-cyclopropyl-3-({3-[(4-methoxypyridin-2-yl) methoxy] benzoyl} amino)-4- methylbenzamide To a stirred solution of N-cyclopropyl-3-[(3-hydroxybenzoyl) amino] -4- methylbenzamide (200 mg, 0.65 mmol) in acetonitrile (50 mL) was added anhydrous potassium carbonate (220 mg, 1.59 mmol) and 4-methoxy-2-chloromethyl-pyridine hydrochloride (150 mg, 0.75 mmol). The mixture was stirred at reflux for 16 hours, then filtered and the solvent evaporated at reduced pressure to give a gum, which was dissolved in ethyl acetate/methanol (19: 1,20 mL) and purified by chromatography on silica, eluting with ethyl acetate/methanol (9: 1) to give the compound as a white solid (250mg, 90%); NMR Spectrum : (CDC13) 0.60 (m, 2H), 0. 80 (m, 2H), 2.32 (s, 3H), 2.86 (m, 1H), 3.85 (s, 3H), 5.19 (s, 2H), 6.67 (s, 1 H), 6.75 (dd, 1H), 7.04 (d, 1H), 7.17 (dd, 1H), 7.21 (d, 1H), 7. 38 (dd, 1H), 7.48 (d, 1H), 7.54 (m, 2H), 8. 02 (s, 1H), 8. 14 (s, 1H), 8. 40 (d, 1H) ; Mass spectrum: M+H+ 432.

Statistics shows that 62734-08-1 is playing an increasingly important role. we look forward to future research findings about 2-(Chloromethyl)-4-methoxypyridine hydrochloride.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/61465; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 10128-72-0, Adding some certain compound to certain chemical reactions, such as: 10128-72-0, name is Methyl 3-hydroxyisonicotinate,molecular formula is C7H7NO3, 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 10128-72-0.

Example A; 3, N-Dihydroxy-isonicotinamide To a stirred suspension of methyl 3-hydroxy-isonicotinate (176 g; 1.15 mol) in water/ice (50/50,1700 mL), was added hydroxylamine hydrochloride (127.9 g; 1.84 mol). The temperature fell to-5 C and then aqueous NAOH solution (454 mL, 28% w/v) was added dropwise keeping the temperature below 5 C during the addition. Hereafter the reaction mixture was stirred at ambient temperature for 1.5 h followed by heating to 60 C. At this temperature the pH was adjusted to 5.4 by the addition of aqueous hydrochloric acid (10 M) at which point a heavy precipitate forms. The reaction mixture was then stirred at ambient temperature followed by cooling to 5 C. THE pH was then adjusted to 4.0 by the addition of aqueous hydrochloric acid (10 M), and then was stirred whilst cold for 1,5 h. The crystals were filtered off, rinsed with water (3 x 100 mL), dried on the filter and then dried further at reduced pressure and 40 C overnight to give 3, N-dihydroxy-isonicotinamide (169.3 g, 96%; HPLC purity 98%) as a white solid. NMR data : H-NMR (DMSO-d6,250 MHz) 8 = 7.55 (1H, d, J=6 Hz); 8.11 (1H, d, J=6 Hz); 8.32 (1H, s); 9.56 (1H, s, broad peak); 11.50 (1H, s, broad peak) ppm.

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. 10128-72-0, Methyl 3-hydroxyisonicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; H. LUNDBECK A/S; WO2005/23820; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13958-86-6, 5-Methylpyridine-3,4-diamine, 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-Methylpyridine-3,4-diamine, blongs to pyridine-derivatives compound. Application In Synthesis of 5-Methylpyridine-3,4-diamine

Aquo composite of 7-methyl-1H-[1,2,3]triazolo[4,5-c]pyridinium nitrate was obtained from 5-methylpyridine-3,4-diamine. 19 mmol (2.4 g) of this substrate were dissolved in 75 mL of water and 3 mL of concentrated H2SO4 acid was added. This solution was cooled to 0 C and then a solution made from 15 mL of water and 30 mmol (2.1 g) of NaNO2 was added dropwise. The mixture was stored at room temperature for 0.5 h, vaporized to its half volume and neutralized with KHCO3. After filtration 1.9 g of powder (melting point 260 C with its decomposition) was obtained. The yield of this synthesis was 73%. The obtained composite was recrystallized from a small amount of water. It is well soluble in water and alcohol but hardly soluble in benzene and chloroform. The transformation process of the cationic unit of the composite is described in Scheme 1 [53].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13958-86-6, 5-Methylpyridine-3,4-diamine, and friends who are interested can also refer to it.

Reference:
Article; Dymi?ska, Lucyna; Sheweshen, Khalil Salem M.; G?gor, Anna; Lorenc, Jadwiga; Hanuza, Jerzy; Journal of Molecular Structure; vol. 1133; (2017); p. 9 – 17;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1149-24-2, 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. 1149-24-2, name is Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate, molecular formula is C13H17NO4, 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.

General procedure: To a mixture of ethyl acetoacetate or methyl acetoacetate (1 eqv), formaldehyde (1.1 eqv) and NH4OAc (1.5 eqv) in acetic acid (3 mL) was added FeWO4 (20 mol%) at room temperature and the mixture was heated at 80 C for 2 h (monitoring by TLC) to give poly-substituted pyridine (3), to this solution isatin (1 eqv) was added and heating continued at same temperature for 3 h (monitoring by TLC). After that the reaction mixture was cooled to room temperature neutralized with sodium bicarbonate and extracted with EtOAc (2 × 10 mL). The organic layers were washed with brine, dried using sodium sulphate .Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography. Elution of the column with petroleum ether-EtOAc gave the desired product.

According to the analysis of related databases, 1149-24-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Paplal, Banoth; Nagaraju, Sakkani; Sathish, Kota; Kashinath, Dhurke; Catalysis Communications; vol. 103; (2018); p. 110 – 115;,
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. 1074-98-2, name is 3-Methyl-4-nitropyridine 1-oxide, molecular formula is C6H6N2O3, 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. HPLC of Formula: C6H6N2O3

Step 2: A solution of 3-methyl-4-nitropyridine /V-oxide (30.0g, 195 mmol) and 10% Pd-C (6.0 g) in EtOH (450 mL) was stirred at rt under H2 (5 bar) for 36 h. The RM was filtered through a pad of celite and the volatiles were removed under reduced pressure to yield the desired compound (20.0 g, 95%).

With the rapid development of chemical substances, we look forward to future research findings about 1074-98-2.

Reference:
Patent; GRUeNENTHAL GMBH; VOSS, Felix; RITTER, Stefanie; NORDHOFF, Sonja; WACHTEN, Sebastian; OBERBOeRSCH, Stefan; KLESS, Achim; WO2015/22073; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 947179-03-5, Adding some certain compound to certain chemical reactions, such as: 947179-03-5, name is Ethyl 4-bromo-6-methylpicolinate,molecular formula is C9H10BrNO2, 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 947179-03-5.

A solution of 4-bromo-6-methyl-pyridine-2-carboxylic acid ethyl ester (2.42 g, 9.91 mmol) in 6 N aq. HCI (100 ml_) is stirred at 65C for 18 h. The solvent is evaporated and the residue is dried under HV, suspended in DCM, filtered and dried again under HV to give 4-bromo-6-methyl-pyridine-2-carboxylic acid (2.50 g) as a hydrochloride salt in form of a white powder; LC-MS: tR = 0.46 min, [M+1]+ = 215.93.

According to the analysis of related databases, 947179-03-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2009/24905; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 127356-38-1, 2-Methoxy-5-nitropyridin-4-amine, 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, 127356-38-1, blongs to pyridine-derivatives compound. Application In Synthesis of 2-Methoxy-5-nitropyridin-4-amine

Step 3: Synthesis of 6-methoxypyridine-3,4-diamine Aq. conc. HCl (1 ml, 32.9 mmol) was diluted with water. To the solution was added tin (II) chloride (0.448 g, 2.365 mmol), followed by 2-methoxy-5-nitropyridin-4-amine (0.1 g, 0.591 mmol). The mixture was heated to 60 C. for 18 h. The reaction mixture was cooled to room temperature, then basified using 10% NaOH solution. The mixture was extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resultant crude compound was triturated with 10% ethyl acetate in Pet-ether to afford 6-methoxypyridine-3,4-diamine (0.06 g, 0.366 mmol, 62.0% yield) as a solid. 1H NMR (400 MHz, DMSO-d6): delta ppm 7.21 (s, 1H), 5.83 (s, 1H), 5.39 (b s, 2H), 4.04 (b s, 2H), 3.62 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,127356-38-1, its application will become more common.

Reference:
Patent; Sun, Li-Qiang; Zhao, Qian; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshim, Pulicharla; Gillis, Eric P.; Scola, Paul Michael; US2014/127156; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem