Sulfuric Acid → 4-Chloro-2,3-dioxo-2,3-dihydro-1H-indole-5-carboxylic acid

HRID 1822897Notes

Reaction equation

HRID 1822897 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([NH:11][C:12](=[O:16])[CH:13]=NO)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)[OH:18]>>[Cl:1][C:2]1[C:3]([C:4]([OH:6])=[O:5])=[CH:7][CH:8]=[C:9]2[C:10]=1[C:13](=[O:18])[C:12](=[O:16])[NH:11]2

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 714168982-Chloro-4-[2-(hydroxyimino)acetamido]benzoic acid

Product 1

HCID 221696584-Chloro-2,3-dioxo-2,3-dihydro-1H-indole-5-carboxylic acid

Conditions

Temperature
80 °C

Procedure

2-chloro-4-[(-2-(hydroxyimino)ethanoyl)amino]benzoic acid (300 mg, 1.24 mmol) was dissolved in concentrated sulfuric acid (5 mL). It was stirred at 80° C. for 3 h. The reaction mixture was cooled to rt, poured into ice water and it was extracted twice with ethylacetate. The title compound was obtained as an orange solid (256 mg, 92%) containing 12% of the regioisomer (6-chloro-2,3-dioxoindoline-5-carboxylic acid).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionwas extracted twice with ethylacetate

Sources & evidence

ORD record
ord-6e17fb545ff6496389bbee0b648089b5
Source dataset
uspto-grants-2006_05
Patent number
US07037909B2

Reaction notes

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