Category: 54221-96-4

Application of 54221-96-4 ,Some common heterocyclic compound, 54221-96-4, molecular formula is C7H7NO2, 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.

6-Methoxy-2-pyridinecarboxaldehyde (1.0 mL, 8.31 mmol) and 2-naphthylamine (1.19 g,8.33 mmol) were dissolved in 25 mL of anhydrous methanol and the resulting mixture washeated at reflux temperature for 6 h. The solvent was removed under reduced pressure togive brown solids. Yield: 1.58 g (72percent). Anal. Calcd (percent) for C17H14N2O (M = 262.31 g mol?1): C,77.84; H, 5.38; N, 10.68. Found: C, 77.88; H, 5.43; N, 10.71. FT-IR (KBr, cm?1): 3439(w), 3051(w),2976(w), 2840(w), 1632(m), 1586(s), 1569(m), 1508(w), 1467(s), 1438(m), 1413(w), 1350(w),1334(m), 1321(m), 1267(s), 1229(w), 1208(w), 1167(w), 1151(m), 1120(w), 1078(w), 1032(m),985(w), 961(w), 911(w), 887(w), 860(s), 824(m), 808(s), 750(s), 734(w), 666(w), 626(w), 603(w),523(w), 504(w), 478(w), 430(w). 1H NMR (400 MHz, CDCl3): delta 8.63 (s, 1H, CH = N), 7.52?7.87(m, 7H, Naphthalene-H), 6.84?7.02 (m, 3H, Py-H3,4,5), 4.03 (s, 3H, ?OCH3) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,54221-96-4, its application will become more common.

Reference:
Article; Dong, Yu-Wei; Wang, Ping; Fan, Rui-Qing; Chen, Wei; Wang, A-Ni; Yang, Yu-Lin; Journal of Coordination Chemistry; vol. 70; 11; (2017); p. 1953 – 1972;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 54221-96-4 ,Some common heterocyclic compound, 54221-96-4, molecular formula is C7H7NO2, 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.

General procedure: To a solution of 6-methoxy-2-pyridinecarboxaldehyde (1.0 eq) in THF (0.05 M) was added dropwise ArMgBr (1.0 M in Et2O, 1.2 eq) at ?78 °C. After stirring at ?78 °C for 1 h, the reaction mixture was quenched by 1 N HCl and extracted with EtOAc. A combined organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography (EtOAc/hexanes).

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. 54221-96-4, 6-Methoxypicolinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fei, Xiang; Yuan, Yue; Lee, Young-Mi; Jeong, Kwang Won; Seo, Seung-Yong; Bulletin of the Korean Chemical Society; vol. 35; 8; (2014); p. 2547 – 2550;,
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.54221-96-4, name is 6-Methoxypicolinaldehyde, molecular formula is C7H7NO2, molecular weight is 137.14, as common compound, the synthetic route is as follows.SDS of cas: 54221-96-4

2-(3,4-dichlorophenyl)acetonitrile (3.50 g, 18.8 mmol) was taken up in THF (30 mL) and diethyl ether (30 mL), and cooled to -78 °C in an acetone-dry ice bath. BuLi (8.1 mL, 20 mmol, 1.6 M in hexane) was added drop-wise, and the temperature was maintained below -60 °C. Once the last drop had been added, the reaction was allowed to stir for 15 minutes. This solution became orange clear. 6- methoxypicolinaldehyde (2.3 mL, 19 mmol) dissolved in THF (20 mL) was added slowly drop-wise, and the temperature was maintained below -60 °C. Solution was dark brown / black clear at this point and was allowed to stir for 1.5 hours at -75 °C. The reaction was quenched with acetic acid (1.6 mL, 28 mmol) dissolved in 5 mL of diethyl ether, added drop-wise while the reaction was cooled in the dry ice acetone bath. The temperature was maintained below -60 °C. LCMS revealed mostly one peak with the desired mass. The reaction was worked up by adding 100 mL of water, and layers were separated. The aqueous phase was extracted with ethyl acetate three times. The combined organic layers were washed with brine, dried over MgSC , and concentrated in vacuo to afford 8.14 grams of a clear amber oil. LCMS revealed a peak that was consistent with desired material. The material was absorbed onto silica gel and ran through an ISCO 80 gram column, eluting with CH2C12 / EtOAc. The broad peak looked to be a mixture of diastereomers in a ratio around 1.5:1. It was not determined which diastereomeric pair is the more predominant pair (0.988 g). The spiked shoulder from that broad peak looked to be a mixture of diastereomers in a ratio around 4: 1 (4.39 g).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,54221-96-4, 6-Methoxypicolinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; MAYO FOUNDATION FOR MEDICAL EDUCATION AND RESEARCH; VIRGINIA TECH INTELLECTUAL PROPERTIES, INC.; RICHELSON, Elliott; FAUQ, Abdul H.; CARLIER, Paul R.; MONCEAUX, Christopher J.; WO2014/159251; (2014); A2;,
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. 54221-96-4, name is 6-Methoxypicolinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 6-Methoxypicolinaldehyde

A solution of 2,6-bis(2,5-dimethyl-1H-pyrrol-1-yl)pyridine (49a, 0.730 g, 2.75mmol) in THF (12.5 mL) was treated with nBuLi (1.15 mL, 2.88 mmol) at 0 °C andstirred for 15-20 mm. To this solution was added 6-methoxypicolinaldehyde (0.343 g, 2.50 mmol). After 1 h, the reaction mixture was extracted from water with EtOAc, concentrated and used as is as the title compound (51b, 1.006 g, 2.500 mmol, contaminated with pyridin-3y1 regioisomer); To a solution of (2,6-bis(2,5-dimethyl- 1H-pyrrol- 1 -yl)pyridin-4-yl)(6-methoxypyridin-2-yl)methanol (51b, 1.006 g, 2.5 mmol) in DCM (12.5 mL) was added acetic anhydride (0.283 mL, 3.00 mmol), DMAP (0.03 1 g, 0.25 mmol) and Et3N (0.418 mL, 3.00 mmol), and the reaction mixture was allowed to stir overnight. The reaction mixture was partitioned between sat aq NaHCO3 and EtOAc. The organics were concentrated, and the residue was purified by silica gel chromatography to furnish thetitle compound (51c, 0.638 g, 1.43 mmol, contaminated with pyridin-3y1 regioisomer); To a solution of (2,6-bis(2,5-dimethyl- 1H-pyrrol- 1 -yl)pyridin-4-yl)(6- methoxypyridin-2-yl)methylacetated (51c, 0.638 g, 1.43 mmol) in THF (14.4 mL) under argon was added 1PrOH (0.166 mL, 2.15 mmol) and Sm12 (57.4 mL, 5.74 mmol), and thereaction mixture was stirred overnight. The reaction mixture was partitioned between brine and EtOAc. The organic layer was concentrated, and the residue was purified by silica gel chromatography to furnish the title compound (51d, 0.448 g, 1.159 mmol, contaminated with pyridin-3y1 regioisomer). MS(ESI) m/z 387.1 (M+H).

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, 54221-96-4, 6-Methoxypicolinaldehyde.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHAW, Scott, A.; SMALLHEER, Joanne, M.; (108 pag.)WO2017/40451; (2017); 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 54221-96-4, name is 6-Methoxypicolinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C7H7NO2

General procedure: The mixture of benzaldehyde (3a) (1 mL, 0.010 mol), 2 (2.45 g,0.010 mol) and triethyl phosphite (4) (3.4 mL, 0.020 mol) was placed in a round bottomed flask. To this mixture, 37percent nano-BF3*SiO2 (0.30g) was added and the mixture was irradiated in the ultrasonicator at ambient temperature for about 10 minutes. The progress of the reaction was monitored by TLC (EtOAc/nhexane7:3). After completion of the reaction as checked byTLC, the reaction mixture was cooled to room temperature. CH2Cl2 (15 mL) was added to the reaction content and stirred for 10 min. The catalyst nano-BF3*SiO2 was separated by filtrationas residue, washed with CH2Cl2 (2 × 10 mL) and the residue was dried under vacuum at 100°C to be utilized in further studies. The combined organic layer was washed with water (15 mL), dried over anhydrous Na2SO4 and concentrated under vacuum at 50°C to obtain crude 5a. Pure 5a was obtained by column chromatography (EtOAc/n-hexane 7:3). The same procedure was used for the preparation of the remaining compounds 5b-k.

With the rapid development of chemical substances, we look forward to future research findings about 54221-96-4.

Reference:
Article; Ravikumar; Mohan; Subramanyam, Ch.; Rao, K. Prasada; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 193; 6; (2018); p. 400 – 407;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 54221-96-4 , The common heterocyclic compound, 54221-96-4, name is 6-Methoxypicolinaldehyde, molecular formula is C7H7NO2, 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.

The general procedure for the synthesis of the 3-aminoindolizine derivatives 1a-e, 6a-g, and uncyclized product 8a-c is described below: To a reaction mixture of cyano substrate 3 (2.0 mmol), 2-carbonyl pyridine derivative (2.0 mmol), and piperidinium acetate (15 mg, 0.10 mmol) in toluene (6 ml), was added diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate (9) (Hantzsch ester, 557 mg, 2.2 mmol) in one portion at room temperature. The resulting mixture was degassed with a stream of nitrogen and then stirred at 105 °C for 3 h. After cooling to room temperature, a minimum amount (ca 0.3-0.5 mL) of DMSO was added to the reaction mixture and the resulting solution was directly loaded to a silica gel column and purified by column chromatography using Teledyne Isco Combiflash system.

The synthetic route of 54221-96-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Lianhai; Chua, Waepril Kimberly S.; Tetrahedron Letters; vol. 52; 12; (2011); p. 1392 – 1394;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 54221-96-4, 6-Methoxypicolinaldehyde, 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, 54221-96-4, blongs to pyridine-derivatives compound. Recommanded Product: 6-Methoxypicolinaldehyde

6-Methoxy-2-pyridinecarboxaldehyde (2.0 mL, 16.63 mmol) and 2,6-dimethylaniline(2.07 mL, 16.74 mmol) were dissolved in 30 mL of anhydrous methanol and the resultingmixture was allowed to stir magnetically for 5 h at room temperature. The solvent wasremoved under reduced pressure to give yellow powders. Yield: 2.53 g (63percent). Anal. Calcd(percent) for C15H16N2O (M = 240.31 g mol?1): C, 74.97; H, 6.71; N, 11.66. Found: C, 74.85; H, 6.72; N,11.62. FT-IR (KBr, cm-1): 3426(w), 3073(w), 2942(w), 2852(w), 1652(s), 1589(s), 1572(m),1539(w), 1466(s), 1443(m), 1412(w), 1378(w), 1334(m), 1324(m), 1267(s), 1232(w), 1195(m),1148(m), 1087(w), 1039(m), 985(w), 958(w), 915(w), 856(m), 805(m), 788(w), 768(s), 739(w),730(w), 690(w), 617(w), 562(w), 511(w), 487(w), 464(w). 1H NMR (400 MHz, CDCl3): delta 8.21 (s,1H, CH = N), 7.85 (d, 1H, Py-H5), 7.71 (t, 1H, Py-H4), 7.58 (d, 1H, Py-H3), 6.85?7.08 (m, 3H,Ph-H3,4,5), 3.99 (s, 3H, ?OCH3), 2.16 (s, 6H, ?CH3) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,54221-96-4, its application will become more common.

Reference:
Article; Dong, Yu-Wei; Wang, Ping; Fan, Rui-Qing; Chen, Wei; Wang, A-Ni; Yang, Yu-Lin; Journal of Coordination Chemistry; vol. 70; 11; (2017); p. 1953 – 1972;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 54221-96-4 ,Some common heterocyclic compound, 54221-96-4, molecular formula is C7H7NO2, 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.

(1)A solution of methylpiperazine (2.31 g) in tetrahydrofuran (20 mL) was cooled to -78° C., and n-butyllithium (2.64 M, 7.55 mL) was added dropwise in an argon gas atmosphere.After stirring at the same temperature for 15 minutes, a solution of 6-methoxypicolinaldehyde (2.5 g) in tetrahydrofuran was added and the mixture was stirred for 30 minutes. t-Butyllithium (1.59 M, 17.1 mL) was added dropwise to the reaction solution, and the mixture was stirred at the same temperature for one hour and at -40° C. for 15 minutes.The reaction solution was cooled again to -78° C. A solution of hexachloroethane (12.9 g) in tetrahydrofuran (20 mL) was slowly added dropwise, and the mixture was stirred at the same temperature for 30 minutes.The reaction solution was poured into water, followed by extraction with ethyl acetate.The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered, after which the filtrate was concentrated under reduced pressure.The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1?10:1) to give 5-chloro-6-methoxypyridine-2-carbaldehyde as a colorless powder (1.21 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,54221-96-4, its application will become more common.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; NISSAN CHEMICAL INDUSTRIES, LTD.; US2011/237791; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 54221-96-4, 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. 54221-96-4, name is 6-Methoxypicolinaldehyde, molecular formula is C7H7NO2, 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: General procedure: 8-Hydrazinocaffeine (3) (112 mg;0.5 mmol) and carbonyl compound (1 mmol; 2 eq.) were mixedin ethanol (20 mL, containing 0.2 mL of acetic acid) and heated at 75 omicronC for 3 days. After cooling down, reaction mixture was evaporatedto dryness and solid residue was suspended in diethyl ether(50 mL), filtered off, washed with additional portion of diethylether (3 25 mL) and dried in vacuo at 50 C to obtain the hydrazone.

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 54221-96-4, 6-Methoxypicolinaldehyde.

Reference:
Article; Kaplanek, Robert; Jakubek, Milan; Rak, Jakub; Kejik, Zden?k; Havlik, Martin; Dolensky, Bohumil; Frydrych, Ivo; Hajduch, Marian; Kola?, Milan; Bogdanova, Kate?ina; Kralova, Jarmila; D?ubak, Petr; Kral, Vladimir; Bioorganic Chemistry; vol. 60; (2015); p. 19 – 29;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem