ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyridine compound Methylpyridine 2-Amino-6-methyl-5-nitropyridine

2-Amino-6-methyl-5-nitropyridine

Product Name2-Amino-6-methyl-5-nitropyridine
CAS22280-62-2
MFC6H7N3O2
MW153.14
EINECS
MOL File22280-62-2.mol

Chemical Properties

Melting point	185-189 °C
Boiling point	276.04°C (rough estimate)
Density	1.3682 (rough estimate)
refractive index	1.6500 (estimate)
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
pka	2.97±0.37(Predicted)
form	Powder
color	Yellow
InChIKey	BGMZTBKXOFFTBJ-UHFFFAOYSA-N
CAS DataBase Reference	22280-62-2(CAS DataBase Reference)

Safety Information

Hazard Codes	Xn,Xi
Risk Statements	36/37/38-20/21/22
Safety Statements	36/37/39-26-22-36
HazardClass	6.1
HS Code	29333999

MSDS

Provider	Language
ACROS	English

Usage And Synthesis

Chemical Properties

Light yellow Cryst

Uses

2-Amino-6-methyl-5-nitropyridine serves as a precursor for synthesizing the imidazo[1,2-a]pyridine derivative 5-methyl-6-nitroimidazo[1,2-a]pyridine via reaction with chloroacetaldehyde in ethanol, and is also employed to construct the 5-substituted pyrrolo[3,2-b]pyridine nucleus[6][7].

Synthesis

1824-81-3

22280-62-2

General procedure for the synthesis of 2-amino-5-nitro-6-methylpyridine from 2-amino-6-methylpyridine: 10 mL of concentrated sulfuric acid was cooled to 0-1 °C and 2-amino-6-methylpyridine (20 g) was slowly added, keeping the temperature at 0 °C. Subsequently, 110 mL of nitric acid in the ratio of 1:1 by volume was slowly added, stirred at -1 °C and continued stirring at room temperature for 30 min. The reaction mixture was warmed up to 50 °C for 11 hours. After completion of the reaction, the reaction solution was extracted with ethyl acetate (EA). The ethyl acetate layer was washed with ammonia and then the ammonia layer was concentrated. Eventually, the solid product 2-amino-5-nitro-6-methylpyridine (18 g) was precipitated in 75% yield.

References

[1] Patent: CN105906621, 2016, A. Location in patent: Paragraph 0019
[2] Patent: WO2005/42464, 2005, A1. Location in patent: Page/Page column 32-33
[3] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 8, p. 1858 - 1868
[4] Patent: WO2009/30725, 2009, A2. Location in patent: Page/Page column 58
[5] Patent: EP1857444, 2007, A1. Location in patent: Page/Page column 20
[6] Andaloussi, M., Moreau, E., Masurier, N., Lacroix, J., Gaudreault, R. C., Chezal, J.-M., Laghdach, A. E., Canitrot, D., Debiton, E., Teulade, J.-C., & Chavignon, O. (2008). Novel imidazo[1,2-a]naphthyridinic systems (part 1): Synthesis, antiproliferative and DNA-intercalating activities. European Journal of Medicinal Chemistry, 43(11), 2505–2517. https://doi.org/10.1016/j.ejmech.2008.02.017
[7] Filla, S. A., Mathes, B. M., Johnson, K. W., Phebus, L. A., Cohen, M. L., Nelson, D. L., Zgombick, J. M., Erickson, J. A., Schenck, K. W., Wainscott, D. B., Branchek, T. A., Schaus, J. M. (2003). Novel Potent 5-HT_1F Receptor Agonists: Structure−Activity Studies of a Series of Substituted N-[3-(1-Methyl-4-piperidinyl)-1H-pyrrolo[3,2-b]pyridin-5-yl]amides. Journal of Medicinal Chemistry, 46(14), 3060–3071. https://doi.org/10.1021/jm030020m

2-Amino-6-methyl-5-nitropyridine

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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