Sodium Hydroxide → 6-Amino-5-fluoroindolin-2-one

HRID 2068733Notes

Reaction equation

HRID 2068733 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([F:9])=[CH:4][C:3]=1[CH2:10][C:11]([OH:13])=O.[OH-].[Na+]>Cl>[NH2:8][C:6]1[C:5]([F:9])=[CH:4][C:3]2[C:2]([CH:7]=1)=[N:1][C:11](=[O:13])[CH:10]=2.[F:9][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][C:6]=1[NH2:8])[NH:1][C:11](=[O:13])[CH2:10]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59250076HCID 59250076, compound

Product 2

HCID 101035046-Amino-5-fluoroindolin-2-oneYield 164.8%HCID 67531248HCID 67531248, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(2,4-Diamino-5-fluoro-phenyl)-acetic acid 9c (7.12 g, 38.7 mmol) was dissolved in 100 mL of hydrochloric acid (1 M) under stirring at room temperature, and the reaction solution was heated to reflux for 1 hour. The reaction was completed until TLC showed the disappearance of starting materials. The reaction mixture was naturally cooled down to room temperature, followed by an ice-water bath cooling, and 100 mL of sodium hydroxide solution (1M) was then added dropwise to neutralize the reaction solution. The mixture was extracted with ethyl acetate (125 mL ×4). The combined organic extracts were washed with saturated brine (100 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound 5-fluoro-6-amino-1,3-dihydro-indol-2-one 9d (5.3 g, yield 82.8%) as a yellow solid.

Workup

  1. temperaturethe reaction solution was heated
  2. temperatureto reflux for 1 hour
  3. temperatureThe reaction mixture was naturally cooled down to room temperature
  4. customfollowed by an ice-water bath
  5. temperaturecooling
  6. extractionThe mixture was extracted with ethyl acetate (125 mL ×4)
  7. washThe combined organic extracts were washed with saturated brine (100 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7bd4fcd178444d4a8eedf324db633693
Source dataset
uspto-grants-2012_10
Patent number
US08299069B2

Reaction notes

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