Nitric Acid → HCID 19737208, compound

HRID 258251Notes

Reaction equation

HRID 258251 reaction equation
[Cl:1][C:2]1[C:3]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=3)[CH:14]=[N:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[N+:24]([O-])([OH:26])=[O:25]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:3]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([N+:24]([O-:26])=[O:25])=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=3)[CH:14]=[N:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 197371941-[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]-6-nitro-1H-indazole

Product 1

HCID 19737208HCID 19737208, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 1-(3-chloro-5-trifluoromethylpyridin-2-yl)-6-nitroindazole [Compound No. 3] (10 g) in conc. sulfuric acid (100 g), fuming nitric acid (3.2 g) was added dropwise while cooling with ice, and the resultant mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was poured into ice water, and precipitated crystals were collected by filtration, washed and dried. The crystals were purified by silica gel column chromatography with hexane-ethyl acetate (4:1) to give 1-(3-chloro-5-trifluoromethylpyridin-2-yl)-5,6-dinitroindazole (8.0 g).

Workup

  1. temperaturewhile cooling with ice
  2. customAfter completion of the reaction
  3. customprecipitated crystals
  4. filtrationwere collected by filtration
  5. washwashed
  6. customdried
  7. customThe crystals were purified by silica gel column chromatography with hexane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-8e36c3400cbf41cd999f842b32d0cc5a
Source dataset
uspto-grants-1993_11
Patent number
US05266556

Reaction notes

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