Sulfuric Acid → 5-Fluoroisatin

HRID 1470591Notes

Reaction equation

HRID 1470591 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:13])[CH:10]=NO)=[CH:4][CH:3]=1.[OH:14]S(O)(=O)=O>>[F:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:8][C:9](=[O:13])[C:10]2=[O:14]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 6400930HCID 6400930, compound

Product 1

HCID 2365665-Fluoroisatin

Conditions

Temperature
80 °C

Procedure

To a hot solution of conc. H2SO4 (20 mL) at 60° C., (N-(4-Fluoro-phenyl)-2-hydroxyimino-acetamide (5 g, 27.0 mmol) was added portion wise. 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.

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-5ea917e6e319484fbe1373ac7a916508
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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