Sulfuric Acid → 5-Bromoisatin

HRID 1470596Notes

Reaction equation

HRID 1470596 reaction equation
[OH:1]S(O)(=O)=O.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:18])[CH:15]=NO)=[CH:9][CH:8]=1>>[Br:6][C:7]1[CH:12]=[C:11]2[C:10](=[CH:9][CH:8]=1)[NH:13][C:14](=[O:18])[C:15]2=[O:1]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 85085907HCID 85085907, compound

Product 1

HCID 68895-Bromoisatin

Conditions

Temperature
80 °C

Procedure

To a hot solution of conc. H2SO4 (48 mL) at 60° C. was added portion wise (N-(4-bromo-phenyl)-2-hydroxyimino-acetamide (12 g, 41.1 mmol). After completion of the addition, the temperature was increased to 80° C. and maintained for one hour. After completion of the reaction, the reaction mixture was poured on to crushed ice and the resulting precipitate was filtered, washed with water (2-3 times) and dried to obtain the title compound as brick red solid (10 g, 89%).

Workup

  1. additionAfter completion of the addition
  2. temperaturemaintained for one hour
  3. customAfter completion of the reaction
  4. additionthe reaction mixture was poured on
  5. customto crushed ice
  6. filtrationthe resulting precipitate was filtered
  7. washwashed with water (2-3 times)
  8. customdried

Sources & evidence

ORD record
ord-4a356616eda1481c8997111d2063689c
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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