Sulfuric Acid → 6-Fluoro-5-methyl-1H-indole-2,3-dione

HRID 2353921Notes

Reaction equation

HRID 2353921 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:14])[CH:11]=NO)[CH:5]=[CH:6][C:7]=1[CH3:8].S(=O)(=O)(O)[OH:16]>>[F:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]2[C:3]=1[C:11](=[O:16])[C:10](=[O:14])[NH:9]2.[F:1][C:2]1[CH:3]=[C:4]2[C:5]([C:11](=[O:16])[C:10](=[O:14])[NH:9]2)=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 72486482HCID 72486482, compound

Product 2

HCID 453821496-Fluoro-5-methyl-1H-indole-2,3-dioneHCID 68679007HCID 68679007, compound

Conditions

Temperature
80 °C

Procedure

Add of N-(3-Fluoro-4-methyl-phenyl)-2-hydroxyimino-acetamide (2.96 g, 15.10 mmol) in small portions at 65° C. to concentrated sulfuric acid (15 mL) and heat the mixture at 80° C. for 10 minutes. Cool to room temperature, pour into ice water (100 mL) and filter the precipitate and wash with water. Dry the solid to yield 4-Fluoro-5-methyl-1H-indole-2,3-dione and 6-Fluoro-5-methyl-1H-indole-2,3-dione.

Workup

  1. temperatureCool to room temperature
  2. filtrationfilter the precipitate
  3. washwash with water
  4. customDry the solid

Sources & evidence

ORD record
ord-d101fb63d6154c3e922525a071b0c34b
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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