HCID 3106275, compound → 3,5-Dinitropyridine

HRID 617370Notes

Reaction equation

HRID 617370 reaction equation
[N+:1]([C:4]1[C:5](NN)=[N:6][CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)([O-:3])=[O:2]>CO.O.C([O-])(=O)C.[Ag+]>[N+:10]([C:8]1[CH:7]=[N:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=1)([O-:12])=[O:11]

Participants

4

Reactant 1

HCID 3106275HCID 3106275, compound

Product 1

HCID 5980543,5-DinitropyridineYield 21.8%

Reagents, catalysts & solvents 2

HCID 11246Silver acetateCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

Silver acetate (2.0 g) was added to a solution of the crude 3,5-dinitro-pyridinyl-hydrazine (2.2 g) in a mixture of methanol:H2O (1:1, 6 ml), and the mixture was stirred at reflux overnight. Solvent was evaporated, then water and conc. NH4OH were added. The mixture was extracted with ethyl ether, the combined extracts were dried over MgSO4, concentrated and purified by column chromatography (5:1 hexane: ethyl acetate) to give the title compound (400 mg) in 21.8% yield. MS (DCI/NH3) m/e: 124 (M-46+1). 1H NMR (CDCl3, 300 MHz) δ: 9.77 (m, 2H), 9.27 (m, 1H).

Workup

  1. temperatureat reflux overnight
  2. customSolvent was evaporated
  3. additionwater and conc. NH4OH were added
  4. extractionThe mixture was extracted with ethyl ether
  5. dry with materialthe combined extracts were dried over MgSO4
  6. concentrationconcentrated
  7. custompurified by column chromatography (5:1 hexane: ethyl acetate)

Sources & evidence

ORD record
ord-25ca1739e32740e497785605c05b1fd6
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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