Sulfuric Acid → 1H-Indole-2,3-dione, 6-bromo-

HRID 2092532Notes

Reaction equation

HRID 2092532 reaction equation
S(=O)(=O)(O)[OH:2].[Br:6][C:7]1[CH:8]=[C:9]([NH:13][C:14](=[O:18])[CH:15]=NO)[CH:10]=[CH:11][CH:12]=1>>[Br:6][C:7]1[CH:8]=[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 6739944Acetamide, N-(3-bromophenyl)-2-(hydroxyimino)-

Product 1

HCID 957161H-Indole-2,3-dione, 6-bromo-Yield 98%

Conditions

Temperature
90 °C

Procedure

To the concentrated sulfuric acid (275 mL) at 50° C. was added N-(3-Bromo-phenyl)-2-hydroxyimino-acetamide (55 g, 0.2272 mol). The temperature was raised to 90° C. and maintained for 3 h. The reaction mixture was added to ice cold water to get yellow precipitate. The precipitate was filtered and dried to get the title compound as a yellow solid [50 g, 98%]. This material was taken to the next step without any further purification.

Workup

  1. temperaturemaintained for 3 h
  2. additionThe reaction mixture was added to ice cold water
  3. customto get yellow precipitate
  4. filtrationThe precipitate was filtered
  5. customdried

Sources & evidence

ORD record
ord-6fce4a40d4314c3693a7e0215463a2bd
Source dataset
uspto-grants-2013_05
Patent number
US08440662B2

Reaction notes

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