Sulfuric Acid → 4,6-dimethyl-1H-indole-2,3-dione

HRID 591778

Reaction equation

HRID 591778 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:14])[CH:11]=NO)[CH:5]=[C:6]([CH3:8])[CH:7]=1.S(=O)(=O)(O)[OH:16]>>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]2[C:3]=1[C:11](=[O:16])[C:10](=[O:14])[NH:9]2

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 53405864N-(3,5-dimethylphenyl)-2-(hydroxyimino)acetamide

Product 1

HCID 23861614,6-dimethyl-1H-indole-2,3-dione

Conditions

Temperature
80 °C

Procedure

N-(3,5-Dimethyl-phenyl)-2-hydroxyimino-acetamide (13.7 g, 71.3 mmol) was added to concentrated sulfuric acid (70 mL) in a 250 mL flask. The reaction mixture was then heated at 80° C. for 30 minutes, then cooled to room temperature, and poured into ice-water (200 mL). The precipitated solid was filtered and washed with water (100 mL) and dried under vacuum to give 4,6-dimethyl-1H-indole-2,3-dione as an orange solid. Yield: 5.53 g (44%).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe precipitated solid was filtered
  3. washwashed with water (100 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-4a90585c46fa49ca940e88ec3a404be4
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Linked notes

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