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

HRID 1449556Notes

Reaction equation

HRID 1449556 reaction equation
[OH:1]S(O)(=O)=O.[CH3:6][C:7]1[CH:8]=[C:9]([NH:14][C:15](=[O:19])[CH:16]=NO)[CH:10]=[C:11]([CH3:13])[CH:12]=1>O>[CH3:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]2[C:8]=1[C:16](=[O:1])[C:15](=[O:19])[NH:14]2

Participants

4

Reactant 2

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

Product 1

HCID 23861614,6-dimethyl-1H-indole-2,3-dioneYield 72.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred warm (60°-70° C.) solution of concentrated H2SO4 (60 mL) and water (6 mL) was added in small portions N-(3,5-dimethylphenyl)-2-(hydroxyimino)acetamide (15.0 g, 78 mM) so that the temperature of the reaction mixture did not exceed 70° C. After the addition was completed, the reaction mixture was heated at 80° C. for 10 min and then cooled and poured onto ice. The resulting mixture was filtered and the collected solids were washed with water and dried to provide the title compound (9.93 g, 72.6%); MS(CI): 176.

Workup

  1. customdid not exceed 70° C
  2. additionAfter the addition
  3. temperaturecooled
  4. additionpoured onto ice
  5. filtrationThe resulting mixture was filtered
  6. washthe collected solids were washed with water
  7. customdried

Sources & evidence

ORD record
ord-1ec850f6e05c48888403093976538546
Source dataset
uspto-grants-1997_02
Patent number
US05599814

Reaction notes

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