1-METHYL-3,5-DINITRO-1H-PYRIDIN-2-ONE Chemical Properties

Melting point:

174-178℃

Boiling point:

289.5±40.0 °C(Predicted)

Density 

1.60

storage temp. 

Store at 0-8℃

pka

-8.36±0.62(Predicted)

form 

powder to crystal

color 

Light orange to Yellow to Green

λmax

308nm(H2O)(lit.)

InChI

InChI=1S/C6H5N3O5/c1-7-3-4(8(11)12)2-5(6(7)10)9(13)14/h2-3H,1H3

InChIKey

QARVELJVEBLWGK-UHFFFAOYSA-N

SMILES

C1(=O)N(C)C=C([N+]([O-])=O)C=C1[N+]([O-])=O

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

HS Code 

2933399990

1-METHYL-3,5-DINITRO-1H-PYRIDIN-2-ONE Usage And Synthesis

Uses

1-Methyl-3,5-dinitro-1H-pyridin-2-one can be used as an organic synthesis intermediate involved in the efficient synthesis of nitrocyclic ether[b]pyridine. It is also a nucleophilic reagent. It reacts with primary amines to produce carbamates in an efficient way without using reducing agents. The electronic defects of the pyridine cation allow this nucleophilic attack.

Synthesis

General procedure for the synthesis of 1-methyl-3,5-dinitro-1H-pyridin-2-one from 1-methyl-2-pyridone: To a stirred mixture of 1-methyl-2-pyridone (33.47 g, 0.306 mol) and concentrated sulfuric acid (300 mL) was added concentrated nitric acid (120 mL) in batches at 100 °C. The reaction mixture was heated at this temperature overnight and then poured into ice (1400 mL). The precipitate was collected by filtration and washed with water to afford 1-methyl-3,5-dinitro-1H-pyridin-2-one (yield: 18.66 g, 30%).1H NMR (400 MHz, CDCl3): δ 9.05 (d, 1H), 8.90 (d, 1H), 3.80 (s, 3H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 20, p. 5392 - 5397
[2] Patent: WO2004/69832, 2004, A2. Location in patent: Page 137-138
[3] Patent: US2011/98311, 2011, A1
[4] Patent: US2012/309758, 2012, A1
[5] Patent: US2015/231142, 2015, A1. Location in patent: Paragraph 0698

1-METHYL-3,5-DINITRO-1H-PYRIDIN-2-ONE(14150-94-8)Related Product Information

• Pyridine
• Tosyl chloride
• 2-Cyanopyridine
• 3-Nitro-2-pyridinol
• 5-AMINO-1-METHYLPYRIDIN-2(1H)-ONE
• 2-HYDROXY-3,5-DINITROPYRIDINE
• 5-NITRO-1-METHYL-2(1H)-PYRIDINONE
• 1-METHYL-3,5-DINITRO-1H-PYRIDIN-2-ONE