Nitric Acid → 5-chloro-7-nitro-1H-indole-2,3-dione

HRID 1470620Notes

Reaction equation

HRID 1470620 reaction equation
[Cl: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>[Cl: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 872035-chloro-1H-indole-2,3-dione

Product 1

HCID 149531845-chloro-7-nitro-1H-indole-2,3-dioneYield 94.11%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 5-chloro-1H-indole-2,3-dione (2.8 g, 15.46 mmol) in conc. H2SO4 (9 mL) was added fuming nitric acid (1.5 mL) very slowly 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 on to 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 (3.2 g, 94.11%) which was used for the next step directly.

Workup

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

Sources & evidence

ORD record
ord-fead1cb55bb94a30a86aaaa79d8db6f0
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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