Ethylene Glycol → HCID 59754762, compound

HRID 1678108Notes

Reaction equation

HRID 1678108 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.O.[CH2:24](O)CO>>[CH3:24][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[N:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8](=[O:17])[CH2:9]2

Participants

6

Reactant 5

HCID 174Ethylene GlycolHCID 962WaterHCID 128841-PhenylisatinHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 59754762HCID 59754762, compound

Procedure

A suspension of 1-phenyl-1H-indole-2,3-dione (1.908 g, 11.83 mmol) in ethylene glycol (30 mL) is treated with powdered potassium hydroxide (1.92 g, 112 mmol), hydrazine hydrate (16.35 mL) and water (4 mL) as described hereinabove. The crude product is purified by flash chromatography eluting with dichloromethane. Product containing fractions are combined, concentrated and the residue is triturated with pentane to afford 5-methyl-1-phenyl-1H-indol-2-one as an off-white solid. MS 224 (M+1)

Workup

  1. customThe crude product is purified by flash chromatography
  2. washeluting with dichloromethane
  3. additionProduct containing fractions
  4. concentrationconcentrated
  5. customthe residue is triturated with pentane

Sources & evidence

ORD record
ord-9e4b99b0853c45be89c9954760d73c92
Source dataset
uspto-grants-2011_08
Patent number
US08008491B2

Reaction notes

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