Nitric Acid → 1,3-Dinitro-1H-pyrazole

HRID 473136Notes

Reaction equation

HRID 473136 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].[N+:9]([O-])([OH:11])=[O:10].C(OC(=O)C)(=O)C>C(O)(=O)C>[N+:9]([N:6]1[CH:7]=[CH:8][C:4]([N+:1]([O-:3])=[O:2])=[N:5]1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 178526745HCID 178526745, compound

Product 1

HCID 232795291,3-Dinitro-1H-pyrazoleYield 97.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred mixture of 3-nitro-1H-pyrazole (3.16 g, 27.9 mmol) in glacial acetic acid (20 mL) at 0° C. was added fuming nitric acid (2.6 mL, 58.69 mmol) dropwise, followed by acetic anhydride (6.6 mL, 69.87 mmol). The mixture was stirred and allowed to warm to rt over 3 h, then poured into ice water (50 mL) and stirred for 20 h. The mixture was extracted with EtOAc combined organic layers were dried over MgSO4, filtered and concentrated to dryness to afford 1,3-dinitro-1H-pyrazole (4.3 g, 97%). 1H NMR (300 MHz, DMSO-d6) δ 8.00 (br s, 1H), 6.44 (br s, 1H).

Workup

  1. stirringstirred for 20 h
  2. extractionThe mixture was extracted with EtOAc combined organic layers
  3. dry with materialwere dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-65720353799b41928323444160a8f50c
Source dataset
uspto-grants-2014_01
Patent number
US08633207B2

Reaction notes

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