Nitric Acid → 5-Fluoro-7-nitroindole-2,3-dione

HRID 1470592Notes

Reaction equation

HRID 1470592 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[O:12].[N+:13]([O-])([OH:15])=[O:14]>OS(O)(=O)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([N+:13]([O-:15])=[O:14])[CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[O:12]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 2365665-Fluoroisatin

Product 1

HCID 167952125-Fluoro-7-nitroindole-2,3-dioneYield 94.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 5-fluoro-1H-indole-2,3-dione (2.5 g, 15.0 mmol) in conc. H2SO4 (9 mL) was added very slowly fuming nitric acid (1.5 mL) at −5 to 0° C. The reaction mixture was stirred at the same temperature for one hour. After completion of the reaction, the reaction mixture was poured onto crushed ice and the resulting precipitate was filtered, washed with water (2-3 times) and dried under vacuum to obtain the title compound as yellow solid (3 g, 94.30%) which was used for the next step directly.

Workup

  1. customAfter completion of the reaction
  2. additionthe reaction mixture was poured
  3. customonto crushed ice
  4. filtrationthe resulting precipitate was filtered
  5. washwashed with water (2-3 times)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-c62581fc360a4378a3109ff931816cfe
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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