5-Iodoisatin → N'-(5-iodo-2-oxoindol-3-yl)-4-phenoxybenzohydrazide

HRID 642037Notes

Reaction equation

HRID 642037 reaction equation
[I: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:13]([C:20]1[CH:29]=[CH:28][C:23]([C:24]([NH:26][NH2:27])=[O:25])=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)(=O)C>[I: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=[N:27][NH:26][C:24](=[O:25])[C:23]1[CH:22]=[CH:21][C:20]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 27603394-Phenoxybenzhydrazide

Product 1

HCID 178517210N'-(5-iodo-2-oxoindol-3-yl)-4-phenoxybenzohydrazideYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Following the general method as outlined in Example 1, into a suspension of 5-iodo-1H-indole-2,3dione in acetic acid was added 4-phenoxybenzohydrazide. After stirring at 100 ° C., the reaction mixture was cooled to rt and a yellow solid precipitated out. Filtration on a fritté, washing with AcOH, water and drying under vacuo at 60° C. overnight gave 4940 mg of the title compound (93%) as a yellow solid in 99.9% purity by HPLC (Rt: 5.13, gradient of 8 min, MaxPlot detection between 230 and 400 nm).

Workup

  1. temperaturethe reaction mixture was cooled to rt
  2. customa yellow solid precipitated out
  3. filtrationFiltration on a fritté
  4. washwashing with AcOH, water
  5. customdrying under vacuo at 60° C. overnight

Sources & evidence

ORD record
ord-c32473d1d6bb455f91d812226b990886
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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