Sulfuric Acid → 6-chloro-7-methyl-1H-indole-2,3-dione

HRID 251936Notes

Reaction equation

HRID 251936 reaction equation
S(=O)(=O)(O)[OH:2].[Cl:6][C:7]1[C:8]([CH3:19])=[C:9]([NH:13][C:14](=[O:18])[CH:15]=NO)[CH:10]=[CH:11][CH:12]=1>>[Cl:6][C:7]1[C:8]([CH3:19])=[C:9]2[C:10]([C:15](=[O:2])[C:14](=[O:18])[NH:13]2)=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 57374294HCID 57374294, compound

Product 1

HCID 45130676-chloro-7-methyl-1H-indole-2,3-dioneYield 56.5%

Conditions

Temperature
80 °C

Procedure

To 2.5 g of concentrated sulfuric acid was added 2.5 g of N-(3-chloro-2-methylphenyl)-2-(hydroxyimino)acetamide at 50° C., and the mixture was stirred at 80° C. for 30 minutes. The reaction mixture was poured into 200 g of ice, and a deposited precipitate was collected by filtration to obtain 1.3 g of 6-chloro-7-methyl-1H-indole-2,3-dione of the formula:

Workup

  1. filtrationa deposited precipitate was collected by filtration

Sources & evidence

ORD record
ord-fe57f814ca4643388a4ed882e1d37ad3
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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