Sulfuric Acid → 5-chloro-1H-indole-2,3-dione

HRID 1470619Notes

Reaction equation

HRID 1470619 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:13])[CH:10]=NO)=[CH:4][CH:3]=1.[OH:14]S(O)(=O)=O>>[Cl:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:8][C:9](=[O:13])[C:10]2=[O:14]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 6400534N-(4-Chlorophenyl)-2-(hydroxyimino)ethanimidic acid

Product 1

HCID 872035-chloro-1H-indole-2,3-dione

Conditions

Temperature
80 °C

Procedure

To a hot solution of conc. H2SO4 (20 mL) at 60° C. was added portion wise N-(4-chloro-phenyl)-2-hydroxyimino-acetamide (5.5 g, 27.0 mmol). After the addition, the temperature was increased to 80° C. and maintained for one hour. After completion of the reaction, the reaction mixture was poured on to crushed ice and the resulting precipitated solid was separated, filtered, washed with water (2-3 times) and dried to obtain the title compound as brick red solid.

Workup

  1. additionAfter the addition
  2. temperaturemaintained for one hour
  3. customAfter completion of the reaction
  4. additionthe reaction mixture was poured on
  5. customto crushed ice
  6. customthe resulting precipitated solid
  7. customwas separated
  8. filtrationfiltered
  9. washwashed with water (2-3 times)
  10. customdried

Sources & evidence

ORD record
ord-2bff98477e874cc98ba6f4fdabaa58ed
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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