Hydrochloric Acid → 1-Phenyloxindole

HRID 1678107Notes

Reaction equation

HRID 1678107 reaction equation
[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=O)[C:8]2=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].O.NN.Cl>C(O)CO.O>[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][C:8]2=[O:17])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 128841-PhenylisatinHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 3147871-PhenyloxindoleYield 90%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent2×

Conditions

Temperature
160 °C

Procedure

To a solution of commercially available 1-phenyl-1H-indole-2,3-dione (10.10 g, 45.7 mmol) in ethylene glycol (125 mL) is added powdered potassium hydroxide (7.4 g, 112 mmol), hydrazine hydrate (16.35 mL) and water (4 mL). The reaction is heated to 160° C. for 1.5 hr after which it is cooled to room temperature, made acidic with conc. hydrochloric acid, diluted with water and the resulting solids are collected by filtration. The solid is washed with water, dissolved in dichloromethane, dried and the solvent removed to give the 1-phenyl-1H-indol-2-one (8.6 g, 90% yield) as a solid.

Workup

  1. temperatureis cooled to room temperature
  2. filtrationthe resulting solids are collected by filtration
  3. washThe solid is washed with water
  4. dissolutiondissolved in dichloromethane
  5. customdried
  6. customthe solvent removed

Sources & evidence

ORD record
ord-25e0c9a205234cc4a4825c042efe5cd2
Source dataset
uspto-grants-2011_08
Patent number
US08008491B2

Reaction notes

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