Ethylene Glycol → HCID 59754762, compound

HRID 751330Notes

Reaction equation

HRID 751330 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-58398c46ccf441ef861092bd710e131b
Source dataset
uspto-grants-2008_07
Patent number
US07405300B2

Reaction notes

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