Sulfuric Acid → 7-Iodoisatin

HRID 1470637Notes

Reaction equation

HRID 1470637 reaction equation
ON=[CH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[I:13])=[O:5].[OH:14]S(O)(=O)=O>>[I:13][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[NH:6][C:4](=[O:5])[C:3]2=[O:14]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 63998232-(Hydroxyimino)-N-(2-iodophenyl)acetamide

Product 1

HCID 40437057-IodoisatinYield 87%

Conditions

Temperature
85 °C

Procedure

2-(hydroxyimino)-N-(2-iodophenyl)acetamide (3.2 g, 0.011 mmol) was added to conc. H2SO4 (15 mL) in small portions at 60° C. The reaction mixture was further heated at 85° C. for 5 h. After the reaction completion, the reaction mixture was cooled to room temperature and poured into crushed ice. A brown color solid product precipitated. It was then filtered and washed with chilled water several times, then dried in a vacuum oven to get 2.9 g of the required product as a red coloured solid (87%).

Workup

  1. temperatureAfter the reaction completion, the reaction mixture was cooled to room temperature
  2. additionpoured
  3. custominto crushed ice
  4. customA brown color solid product precipitated
  5. filtrationIt was then filtered
  6. washwashed with chilled water several times
  7. customdried in a vacuum oven

Sources & evidence

ORD record
ord-1b14c10ffc9f42068fb6b542d51a8c66
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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