Category: 504-24-5

Electric Literature of 504-24-5, 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 504-24-5 as follows.

A. 3-Iodopyridin-4ylamine. A solution of potassium iodide (19.48 g, 117.4 mmol) and iodine (18.37 g, 72.3 mmol) in water (77 ML) is added dropwise via an addition funnel to a refluxing solution of 4-aminopyridine (9.21 g, 97.8 mmol) and sodium carbonate (6.12 g, 57.7 mmol) in water (35 ML).Upon complete addition the mixture is stirred for 2 hours at reflux then cooled to room temperature and extracted with ethyl acetate.The combined organic layers are washed with saturated sodium thiosulfate solution (3*) and brine then dried over MgSO4, filtered and concentrated to give the title product (8.37 g, 38.0 mmol) and a trace of the di-iodo compound as an yellow/orange solid.This material is used in the subsequent step without further purification. 1H NMR (CDCl3, 300 MHz) delta8.70 (s, 1H), 8.10 (d, 1H), 6.55 (d, 1H), 4.60 (bs, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,504-24-5, its application will become more common.

Reference:
Patent; AVENTIS PHARMACEUTICALS INC.; US2004/102450; (2004); 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. 504-24-5, name is 4-Aminopyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C5H6N2

Example 25A 2,2-dimethyl-N-pyridin-4-ylpropanamide A mixture of 4-aminopyridine (10 g, 106 mmol) and pivaloyl chloride (12.9 g, 107 mmol) in 200 mL dichloromethane was cooled to 0 C. and treated slowly with triethylamine (10.9 g, 108 mmol), warmed to room temperature, stirred overnight, and diluted with water. The aqueous layer was extracted three times with dichloromethane and the combined extracts were washed with brine, dried (Na2SO4), filtered, and concentrated. The product was recrystallized from toluene to provide the desired product (14 g, 74%).

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, 504-24-5, 4-Aminopyridine.

Reference:
Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert B.; Dinges, Jurgen; Hutchins, Charles W.; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/199511; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 504-24-5, 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. 504-24-5, name is 4-Aminopyridine, molecular formula is C5H6N2, 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.

4-OAP was prepared using the Chichibabin reactionof 4-aminopyridine (4-AP) and sodium amide indry dioxane, followed by alkylation with octyl iodide[25]. 4-OAP was isolated from the reaction mixture viaextraction with hexane and recrystallized first fromhexane and then from acetone (99.9%, m.p. 64 ±0.2C). The molecular and structural formulas wereconfirmed via elemental analysis plus IR and 1HNMR spectroscopy. OAP chloride was prepared byshaking a 0.1 M solution of 4-OAP (100 mL) with 1 MHCl (100 mL). The organic phase was separated andfiltered through a paper filter. All chloroform wasevaporated under an air stream. The residue was driedat 60C. The yield was 95%. According to the datafrom potentiometric titration, the content of the mainsubstance was 99.8%.

According to the analysis of related databases, 504-24-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Borshch; Ageeva; Frolova, A. Yu.; Russian Journal of Physical Chemistry; vol. 93; 5; (2019); p. 828 – 834; Zh. Fiz. Khim.; vol. 93; 5; (2019); p. 661 – 667,7;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 504-24-5, 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 504-24-5, name is 4-Aminopyridine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 6 Compounds of the following general formula II-6 may be synthesised, for example, by the following methods. 3-Bromo-4-aminopyridine (1). 4-Aminopyridine (3.0 g, 31.9 mmol) was dissolved in 100 mL of DCM and 60 mL CH3CN. Bromine (5.1 g, 31.9 mmol) was added to this solution dropwise and the solution was stirred for 2 h. Sodium carbonate (6.2 g, 73.8 mmol) was added to the mixture and the reaction was stirred overnight. TLC (EtOAc) analysis of the reaction mixture showed two major spots, the higher running was 4-amino-3,5-dibromopyridine and the lower running one was the desired product (Rf=0.4, EtOAc). The reaction mixture was filtered and the filtrate was concentrated and chromatographed on a minimum amount of silica gel to yield 1.4 g (26%) of the desired product. 1H NMR (CDCl3): delta 8.39 (s, 1H), 8.10 (d, 1H), 6.60 (d, 1H), 4.74 (bs, 2H).

According to the analysis of related databases, 504-24-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ferraris, Dana V.; Li, Jia-He; Kalish, Vincent J.; Zhang, Jie; US2003/22883; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 504-24-5, 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. 504-24-5, name is 4-Aminopyridine. A new synthetic method of this compound is introduced below.

(1) Bromination reaction:In a 100 ml three-necked flask, 3.76 g (0.04 mol)4-aminopyridineAnd 0.04 g of azobisisobutyronitrile were dissolved in 36 ml of carbon tetrachloride,14.95g (0.084mol) of N-bromosuccinimide was added portionwise at 25 C, the reaction was carried out for 20h,After the liquid-phase central control monitored the conversion of 4-aminopyridine and intermediate 3-bromo-4-aminopyridine into the target product 3,5-dibromo-4-aminopyridine,The reaction mixture was cooled to room temperature with stirring, poured into 50ml carbon tetrachloride and stirred, filtered, the filter cake was washed twice with 2 × 30ml carbon tetrachloride, the filtrate was washed once with aqueous sodium bicarbonate solution, saturated salt Water once, spin-dried to remove carbon tetrachloride, and then recrystallized from petroleum ether,9.28 g of a white solid was obtained,Namely 3,5-dibromo-4-aminopyridine,Yield 92.10%

At the same time, in my other blogs, there are other synthetic methods of this type of compound,504-24-5, 4-Aminopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Wohua Chemical Co., Ltd.; Hu Yadong; Yang Benmei; (5 pag.)CN106957259; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 504-24-5, 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.504-24-5, name is 4-Aminopyridine, molecular formula is C5H6N2, molecular weight is 94.12, as common compound, the synthetic route is as follows.

To a solution of 4-aminopyridine (50.0 g, 531 mmol) in triethylamine/CH2Cl2 (1:1, 200 mL) at 0°C was slowly added a solution of di-t-butyl-dicarbonate (116 g, 531 mmol) in CH2Cl2 (150 mL). The resulting mixture was allowed to warm to it overnight then was concentrated. The crude product was taken up in hot EtOAc, filtered and precipitated with hexanes. The precipitate was collected by filtration, washed with hexanes and dried under vacuum to give 91.0 g (88percent yield) of pure t-butyl carbamate.

The chemical industry reduces the impact on the environment during synthesis 504-24-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PURDUE RESEARCH FOUNDATION; WO2007/61554; (2007); A2;,
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. 504-24-5, name is 4-Aminopyridine, molecular formula is C5H6N2, 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-Aminopyridine

To a solution of 4-aminopyridine (1a, 37.65 g, 0.4 mole) in HOAc (200 mL) was added iodine monchloride (130 g, 0.8 mole) portionwise. The reaction mixture was stirred at 45 C. for 20 h, then diluted with water (500 mL). The mixture was cooled to 0 C., and basified 30% NaOH to pH=9-10. The solution was extracted with EtOAc (1 L¡Á2) and the combined extracts were washed with 15% Na2S2O3 (400 mL¡Á2), water, brine, dried over Na2SO4, and evaporated in vacuo to give 1b (62 g) as a light yellow solid. ES-MS m/z 221 (MH+). [0185] Into a pressure flask was added 1b (4.4 g, 20 mmol), cupric iodide (228 mg, 1.2 mmol), (trimethylsilyl)acetylene (7.08 g, 72 mmol), triethylamine (200 mL) and DMF (80 mL). The mixture was stirred under nitrogen for 10 min, followed by addition of Pd(PPh3)2Cl2 (0.84 g, 1.2 mmol). The mixture was then stirred to 70 C. for 5 h, and then diluted with ethyl acetate (600 mL). The solution was washed with H2O (250 mL¡Á2), brine (250 mL), dried over Na2SO4, and evaporated in vacuo to give crude product which was purified by flash chromatography (100% CH2Cl2 to 2% MeOH in CH2Cl2) to afford Compound 1c (2. 97 g, 78%) as a light brown solid. 1H NMR (CDCl3) delta 8.37 (s, 1H), 8.13 (d, J=5.7 Hz, 1H), 6.53 (d, J=5.6 Hz, 1H), 4.67 (bs, 2H), 0.27 (s, 9H). ES-MS m/z 191 (MH+). [0186] Into an ice-cold solution of 1c (1.35 g, 7.1 mmol) in THF (50 mL) was added 95% NaH (1.86 g, 8.5 mmol). The mixture was stirred at 0 C. for 10 min, rt for 10 min, then cooled back to 0 C. (Boc)2O (1.86 g, 8.5 mmol) was added and the mixture was stirred at 0 C. for 30 min and then rt for 2 h. Additional 95% NaH (0.08 g, 3.5 mmol) and (Boc)2O (0.2 g, 0.92 mmol) were added and the mixture was stirred at rt for another 2 h. The reaction was then quenched slowly with saturated NaHCO3 (10 mL), extracted with ethyl acetate (200 mL¡Á2). The organic layer was washed with brine, dried over Na2SO4, and evaporated in vacuo. The crude product was purified by flash chromatography (EtOAc/hexane; 1:3) to give 1d (0.67 g). ES-MS m/z 219 (MH+). [0187] To a solution of 1d (1.3 g, 4.5 mmol) in DMF (20 mL) was added cupric iodide (0.85 g, 4.5 mmol). The mixture was stirred at 80 C. for 6 h and then filtered. The filtrate was extracted with ethyl acetate (100 mL¡Á3), and the organic layer was washed with H2O, brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (Ethyl acetate/hexane; 1:3) to give Compound 1e (0.25 g, 26%). 1H NMR (CDCl3) delta 8.89 (s, 1H), 8.47 (d, J=5.8 Hz, 1H), 7.98 (d, J=5.7 Hz, 1H), 7.62 (d, J=3.7 Hz, 1H), 6.66 (d, J=3.7 Hz, 1H), 1.69 (s, 9H). ES-MS m/z 219 (MH+). [0188] To a solution of 1e (0.178 g, 0.82 mmol) in methylene chloride (5 mL) was added TFA (1.0 mL) slowly. The mixture was stirred at rt for 1.5 h, and The solvent was evaporated to obtain 5-azaindole 1f as a white solid (0.18 g, 95%). 1H NMR (CDCl3) delta 8.97 (s, 1H), 8.31 (d, J=5.7 Hz, 1H), 7.35 (d, J=5.7 Hz, 1H), 7.29 (m, 1H), 6.68 (d, J=3.3 Hz, 1H). ES-MS m/z 119 (MH+). [0189] A mixture of Compound 1f (0.26 g, 2.2 mmol) and cesium carbonate (1.43 g, 4.4 mmol) in DMF (10 mL) was stirred at rt for 10 min, and then 3-methoxypropylbromide (0.40 g, 2.64 mmol) was added. The reaction mixture was stirred at 60 C. for 3 h. The solvent was evaporated and the residue was partitioned between EtOAc (150 mL) and water (100 mL). The organic layer was washed with water (3¡Á50 mL), brine (2¡Á50 mL), then dried (Na2SO4) and evaporated in vacuo to give a brown oil. The crude product was purified by flash column chromatography (from 100% DCM to DCM/MeOH/NH4OH; 97:3:0.3) to afford Compound 1g (0.26 g, 62%) as light brown oil. 1H NMR (CDCl3) delta 8.91 (s, 1H), 8.31 (d, J=5.8 Hz, 1H), 7.27 (s, 1H), 7.11 (d, J=3.2 Hz, 1H), 6.60 (d, J=3.3 Hz, 1H), 4.25 (t, J=6.7 Hz, 2H), 3.32 (s, 3H), 3.25 (t, J=5.7 Hz, 2H), 2.05 (m, 2H). ES-MS m/z 191(MH+). [0190] Oxalyl chloride (3 mL) was added slowly to a solution of compound 1g (0.22 g, 1.14 mmol) in ether (5 mL). The mixture was heated to 48 C. in a pressure tube overnight. TLC shown that some starting materials were still present. Additional 0.5 mL of oxalyl chloride was added and stirring was continuted at 48 C. for another night. The mixture was then cooled down to rt, to which methanol (3 mL) was added. The mixture was heated to 48 C. and stirred for 2 h. The volatiles removed under vacuo and the residue was purified by flash chromatography (from 100% DCM to DCM/MeOH/NH4OH; 97:3:0.3) to afford Compound 1h (0.15 g, 48%) as a white solid. 1H NMR (CDCl3) delta 8.51 (d, J=5.8 Hz, 1H), 8.44 (s, 1H), 7.37 (m, 1H), 4.34 (t, J=6.8 Hz, 2H), 3.97 (s, 3H), 3.35 (s, 3H), 3.30 (t, J=5.7 Hz, 2H), 2.12 (m, 2H). ES-MS m/z 277 (MH+). [0191] The alpha-ketoester Compound 1h (53.8 mg, 0.20 mmol) and amide Compound 1i (23 mg, 0.14 mmol) were combined in dry THF (3 mL) under argon and cooled with an ice bath as a solution of 1.0 M potassium t-butoxide in THF (1 mL, 1 mmol) was added dropwise. The mixture was stirred at 0 C. for 30 …

With the rapid development of chemical substances, we look forward to future research findings about 504-24-5.

Reference:
Patent; Zhang, Han-Cheng; Maryanoff, Bruce E.; Ye, Hong; US2004/192718; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem