HCID 3106275, compound → 3,5-Dinitropyridine

HRID 1416661Notes

Reaction equation

HRID 1416661 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].C(O)=O.C=O>CO.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

5

Reactant 2

HCID 3106275HCID 3106275, compoundHCID 18761834Formaldehyde formic acid

Product 1

HCID 5980543,5-DinitropyridineYield 21.8%

Reagents, catalysts & solvents 2

HCID 11246Silver acetateCatalystHCID 887MethanolSolvent

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, 300MHz) 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-6ff30fc9ce5c4ac4b557e3ed9a283134
Source dataset
uspto-grants-1999_06
Patent number
US05914328

Reaction notes

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