Nitric Acid → HCID 18913969, compound

HRID 1080385Notes

Reaction equation

HRID 1080385 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:11]([Cl:12])=[C:10]([O:13][CH:14]([F:16])[F:15])[N:9]([CH3:17])[N:8]=2)[N:5]=[CH:4][CH:3]=1.[C:18]([O:21]C(=O)C)(=O)[CH3:19].[N+:25]([O-])([OH:27])=[O:26]>C(O)(=O)C>[Cl:12][C:11]1[C:7]([N:6]2[C:2]([NH:1][C:18](=[O:21])[CH3:19])=[C:3]([N+:25]([O-:27])=[O:26])[CH:4]=[N:5]2)=[N:8][N:9]([CH3:17])[C:10]=1[O:13][CH:14]([F:15])[F:16]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 54185846HCID 54185846, compound

Product 1

HCID 18913969HCID 18913969, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.3 g (5.0 mmol) 5-Amino-1-(4-chloro-5-difluoromethoxy-1-methyl-3-pyrazolyl)pyrazole was dissolved in 20 ml acetic acid and treated with 0.55 g (5.4 mmol) acetic anhydride. After stirring for 2 hours at room temperature the reaction solution was cooled to 0° C. and 0.4 g (6.4 mmol) concentrated nitric acid added. After stirring for 8 hours at room temperature, the reaction mixture was poured into ice water and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate 1:1).

Workup

  1. temperaturewas cooled to 0° C.
  2. stirringAfter stirring for 8 hours at room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-4e5b11a372634870916dff8e0945b64a
Source dataset
uspto-grants-1996_12
Patent number
US05580986

Reaction notes

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