100367-40-6 | Pyridine-derivatives

Share a compound : 2-Amino-5-bromo-4-methyl-3-nitropyridine

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100367-40-6, 2-Amino-5-bromo-4-methyl-3-nitropyridine, and friends who are interested can also refer to it.

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.100367-40-6, name is 2-Amino-5-bromo-4-methyl-3-nitropyridine, molecular formula is C6H6BrN3O2, molecular weight is 232.04, as common compound, the synthetic route is as follows.name: 2-Amino-5-bromo-4-methyl-3-nitropyridine

This reaction was conducted under inert gas protection. The reaction vessel was first charged with 2000 ml methanol and cooled to about 0 C. with slight agitation. Then 9.1 kg acetyl chloride was added. The exothermic reaction was then cooled and agitated for 10 minutes. The next addition was 100 g 2-amino-5-bromo-3-nitro-4-picoline (the compound of formula 2 at 0 C. Then 236.5 g of t-butyl nitrite was added at a rate such that the temperature did not exceed 5 C. The slight evolution of nitrogen gas was noted. After the completion of the reaction, cooling was removed and the reaction mixture within the vessel was allowed to warm to 25 C. in about 30 minutes. The mixture was agitated at 25 C. for about 3-4 hours. After 4-5 hours a clear solution was obtained. Reaction completeness was monitored by HPLC after about 4 hours. The reaction was complete after about 5 hours. The reaction mixture was concentrated in vacuo to about 1000 mL. Then 500 ml of water was added and the product precipitated. Then 250 ml saturated sodium bicarbonate solution was added with good agitation to neutralize the HCl and dissolve the hydroxy impurity. The mixture was agitated at 20-25 C. for about 15 minutes and then the precipitate was collected and washed with 1000 ml of water. The product was then dried at 40 C. in vacuo. Yield was 75.0 g. Analytical data: m.p. 132 C. IR (KBr, cm-1): 1633, 1581, 1538, 1512, 1458, 1377, 1344, 1321, 1244, 869, 779. 1H-NMR (DMSO-d6) (delta, ppm): 2.31 (s, 3H), 3.96 (s, 3H), 8.55 (s, 1H): 13C-NMR (DMSO-d6) (delta, ppm): 17.49, 54.91, 99.41, 114.39, 141.02, 149.23, 153.46; HRMS calcd for C7H7BrN2O3 245.96401 found (M+1): 246.97184; Elemental Analysis: calcd for C7H7BrN2O3: C 34.03, H 2.85, N 11.34; found: C 33.81, H 2.91, N 11.24.

Reference:
Patent; Liu, Wansheng; Patel, Sunil S.; Cuniere, Nicolas; Lear, Yvonne; Deshpande, Prashant P.; Simon, Jeffrey N.; Lai, Chiajen; Pullockaran, Annie J.; Soundararajan, Nachimuthu; Bien, Jeffrey T.; US2007/32503; (2007); A1;,
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Pyridine | C5H5N – PubChem

Analyzing the synthesis route of 100367-40-6

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, 100367-40-6, 2-Amino-5-bromo-4-methyl-3-nitropyridine.

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. 100367-40-6, name is 2-Amino-5-bromo-4-methyl-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 2-Amino-5-bromo-4-methyl-3-nitropyridine

Thereafter, this compound is then reacted with sodium nitrite (NaN02) andtrimethylsilyl chloride (T -C1) in methanol (MeOH) to yield .

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; TRIPP, Jonathan Clive; FANFAIR, Dayne Dustan; SCHULTZ, Mitchell J.; MURUGESAN, Saravanababu; FOX, Richard J.; CHEN, Chung-Pin H.; IVY, Sabrina E.; PAYACK, Joseph Francis; DOUBLEDAY, Wendel W.; WO2012/106189; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Introduction of a new synthetic route about 100367-40-6

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. 100367-40-6, name is 2-Amino-5-bromo-4-methyl-3-nitropyridine. A new synthetic method of this compound is introduced below., Computed Properties of C6H6BrN3O2

To a solution of 5-bromo-4-methyl-3-nitropyridin-2-amine (28 g, 121 mmol) in water (900 ml) was added H2S04 (28 ml) followed by NaN02 (20.91 g, 303 mmol) in water (100 ml) drop wise at 0C. The reaction mixture was slowly warmed to room temperature for 2h, the reaction mixture was heated at 100C for 4h. The solid formed in reaction mixture was filtered and dried to afford title compound as a pale yellow solid (24.0 g, 85 %); 1H NMR (400 MHz, DMSO-de) delta 12.97 (s, 1H), 8.01 (s, 1H), 2.21 (s, 3H); LC/MS: 233 (M+l)+.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; BORUAH, Anima; CHITTY VENKATA, Srikanth; HOSAHALLI, Subramanya; PANIGRAHI, Sunil Kumar; WO2014/125408; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem