Hydrochloric Acid → 5-fluoro-1,3-dihydro-2H-indol-2-one

HRID 1888976Notes

Reaction equation

HRID 1888976 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.O.NN.Cl>O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 2365665-Fluoroisatin

Product 1

HCID 37310125-fluoro-1,3-dihydro-2H-indol-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
105 °C

Procedure

Into a 10-L four necked round-bottomed flask equipped with a mechanical stirrer, a thermometer pocket, and a reflux condenser were charged 5-fluoro-isatin (0.3 Kg; 1.81 mole) and 90% hydrazine hydrate. (1.5 Lt) and stirred well for 30 minutes. The temperature of the reaction mixture was raised to 100-110° C. and maintained for 1 hour and the temperature further raised to 125-130° C. and maintained for 4 hours. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mixture was cooled to 25-30° C. and diluted with water. The pH was adjusted with conc. HCl to 3.0. The solution was stirred at 25-30° C. for 4 hours. The product was isolated by filtration and washed with ice water. The product was dried at 60° C.

Workup

  1. temperaturemaintained for 1 hour
  2. temperaturethe temperature further raised to 125-130° C.
  3. temperaturemaintained for 4 hours
  4. customAfter completion of reaction
  5. temperaturethe reaction mixture was cooled to 25-30° C.
  6. stirringThe solution was stirred at 25-30° C. for 4 hours
  7. customThe product was isolated by filtration
  8. washwashed with ice water
  9. customThe product was dried at 60° C.

Sources & evidence

ORD record
ord-02c4811c82c04747b38792569efe6c5d
Source dataset
uspto-grants-2013_08
Patent number
US08501962B2

Reaction notes

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