Category: 6635-86-5

Synthetic Route of 6635-86-5, 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. 6635-86-5, name is 2-Amino-4-methyl-3-nitropyridine, molecular formula is C6H7N3O2, 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.

To a solution of 4-methyl-3-nitropyridin-2-amine (25 g, 163 mmol) in AcOH (250 ml) was added NaOAc (26.7 g, 326 mmol) and cooled to 15-20C. Bromine (78.24 g, 489 mmol) in AcOH (200 ml) was added over 30 min and stirred at room temperature for a period of 2 h. The reaction mixture was poured into ice water, the solid formed was filtered and dried to afford title compound as a yellow solid (32 g, 84 %); 1H NMR (400 MHz, DMSO-d6) delta 8.28 (s, 1H), 7.05 (s, 2H), 2.31 (s, 3H).

According to the analysis of related databases, 6635-86-5, the application of this compound in the production field has become more and more popular.

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

Electric Literature of 6635-86-5, 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. 6635-86-5, name is 2-Amino-4-methyl-3-nitropyridine, molecular formula is C6H7N3O2, 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.

Part A:; A reaction vessel was purged with inert gas. All steps were performed under inert gas protection. The vessel was then charged with 7.50 L of acetic acid at 20-25 C. Next, 1.00 kg of the compound of formula 1 was added to the vessel. A yellow suspension was formed. This was followed by the addition of 1.07 kg of sodium acetate. A very thick, yellow suspension was formed and the reaction was noted to be slightly exothermic. The temperature was raised to about 27 C. The mixture was then cooled to about 15-20 C. and a sample was taken for high pressure liquid chomatography (HPLC) monitoring. A solution of 1.15 kg of bromine (1.1 eq.) and 2.5 L of acetic acid was prepared. A 10/11 portion of the solution, i.e., 1.0 eq. at 15-20 C. was added to the vessel over about 10-15 minutes. The addition was slightly exothermic and some cooling was necessary (Tmax=20 C.). HPLC was used to monitor the reactions progress immediately after the addition and then at 60 min. Less than 10% of the starting material was observed. Then the remainder of the solution was added and the reaction mixture stirred until completion, approximately 30-60 additional minutes. After the reaction was complete 10.0 L of ice water was added, dropping the temperature to 11 C. and forming a suspension. The suspension was stirred for another 30-60 minutes and the product was filtered, then washed with 3×2.50 L of ice water. The product was dried at 40 C. to a constant LOD. The yield was 1.45 kg (96%), yellow crystals. mp. 132 C. IR (KBr, cm-1): 1633, 1581, 1538, 1512, 1458, 1377, 1344, 1321, 1244, 869, 779. 1H-NMR (CDCl3) (delta, ppm): 2.55 (s, 3H), 5.85 (bs, 2H), 8.25 (s, 1H): 13C-NMR (CDCl3) (delta, ppm): 20.81, 112.14, 144.49, 151.91, 153.78 (2C); MS; (M+1): 232; Elemental Analysis: calcd for C6H6BrN3O2: C, 31.05; H, 2.60; N, 18.11; Br, 34.43; found: C, 30.95; H, 2.42; N, 17.45; Br, 34.80.

According to the analysis of related databases, 6635-86-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; US2006/293304; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 6635-86-5, 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. 6635-86-5, name is 2-Amino-4-methyl-3-nitropyridine, molecular formula is C6H7N3O2, 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.

Part A:; A reaction vessel was purged with inert gas. All steps were performed under inert gas protection. The vessel was then charged with 7.50 L of acetic acid at 20-25 C. Next, 1.00 kg of the compound of formula 1 was added to the vessel. A yellow suspension was formed. This was followed by the addition of 1.07 kg of sodium acetate. A very thick, yellow suspension was formed and the reaction was noted to be slightly exothermic. The temperature was raised to about 27 C. The mixture was then cooled to about 15-20 C. and a sample was taken for high pressure liquid chomatography (HPLC) monitoring. A solution of 1.15 kg of bromine (1.1 eq.) and 2.5 L of acetic acid was prepared. A 10/11 portion of the solution, i.e., 1.0 eq. at 15-20 C. was added to the vessel over about 10-15 minutes. The addition was slightly exothermic and some cooling was necessary (Tmax=20 C.). HPLC was used to monitor the reactions progress immediately after the addition and then at 60 min. Less than 10% of the starting material was observed. Then the remainder of the solution was added and the reaction mixture stirred until completion, approximately 30-60 additional minutes. After the reaction was complete 10.0 L of ice water was added, dropping the temperature to 11 C. and forming a suspension. The suspension was stirred for another 30-60 minutes and the product was filtered, then washed with 3×2.50 L of ice water. The product was dried at 40 C. to a constant LOD. The yield was 1.45 kg (96%), yellow crystals. mp. 132 C. IR (KBr, cm-1): 1633, 1581, 1538, 1512, 1458, 1377, 1344, 1321, 1244, 869, 779. 1H-NMR (CDCl3) (delta, ppm): 2.55 (s, 3H), 5.85 (bs, 2H), 8.25 (s, 1H): 13C-NMR (CDCl3) (delta, ppm): 20.81, 112.14, 144.49, 151.91, 153.78 (2C); MS; (M+1): 232; Elemental Analysis: calcd for C6H6BrN3O2: C, 31.05; H, 2.60; N, 18.11; Br, 34.43; found: C, 30.95; H, 2.42; N, 17.45; Br, 34.80.

According to the analysis of related databases, 6635-86-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; US2006/293304; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem