ChemicalBook CAS DataBase List 2-Amino-6-methoxy-3-nitropyridine

2-Amino-6-methoxy-3-nitropyridine synthesis

12synthesis methods

Product Name:2-Amino-6-methoxy-3-nitropyridine
CAS Number:73896-36-3
Molecular formula:C6H7N3O3
Molecular Weight:169.14

124-41-4

27048-04-0

73896-36-3

1. 7.78 g (0.144 mol) of sodium methanolate was mixed with 50.0 mL of methanol and the mixture was cooled to 15 °C. 2. 25.0 g (0.144 mol) of 2-amino-6-chloro-3-nitropyridine was slowly added to the above solution while maintaining 15°C. 3. the reaction mixture was heated to 25°-30°C and stirred continuously at this temperature for 4-5 hours. 4. The progress of the reaction was monitored by thin layer chromatography (TLC). 5. Upon completion of the reaction, the reaction mixture was slowly poured into water to precipitate the product. 6. The precipitate was collected by filtration and washed with cold water. 7. After drying, 21.0 g of 2-amino-3-nitro-6-methoxypyridine was obtained in 86.5% yield and 99.0% purity by HPLC. 8. 8. The melting point of the product was 167°-169°C. 9. 9. 1H-NMR (CDCl3) data: δ 3.89 ppm (single peak, 3H, OCH3), 6.14-6.16 ppm (twin peaks, 1H), 8.24-8.27 ppm (twin peaks, 1H), 8.16 ppm (single peak, 2H, -NH2).

124-41-4 Synthesis

124-41-4
724 suppliers
$12.00/25g

27048-04-0 Synthesis

27048-04-0
348 suppliers
$5.00/250mg

73896-36-3
234 suppliers
$9.00/10g

Yield: 86.5%

Reaction Conditions:

in methanol at 15 - 30; for 4 - 5 h;

Steps:

3 Synthesis of 2-amino-6-methoxy-3-nitropyridine
Sodium methoxide, 7.78 gm (0.144 mole) and methanol 50.0 ml were mixed and cooled to 15° C. To this solution, 25.0 gm of 2-amino-6-chloro-3-nitropyridine (0.144 mole) was added while maintaining the temperature at 15° C. by external cooling. The resulting mixture was heated to 25°-30° C. and maintained at this temperature for 4-5 hrs with constant stirring. The completion of reaction was monitored by TLC. After the completion of reaction, the reaction mixture was poured in water. The precipitate thus obtained was filtered and washed with water. On drying 21.0 gm of 2-amino-3-nitro-6-methoxypyridine (86.5% yield) was obtained, with the HPLC purity of 99.0%. Melting point 167°-169° C.; ¹H-NMR (CDCl₃) δ 3.89 ppm (s,-3H, OCH3), 66.14-6.16 ppm (d, 1H), 68.24-8.27 ppm (d, 1H), 68.16 ppm (s, -2H, -NH₂).

References:

JUBILANT ORGANOSYS LIMITED US2006/80790, 2006, A1 Location in patent:Page/Page column 3

38533-61-8 Synthesis