5-Iodoisatin → HCID 178517199, compound

HRID 642054Notes

Reaction equation

HRID 642054 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:21]=[C:22]([CH:27]=[CH:28][CH:29]=1)[C:23]([NH:25][NH2:26])=[O:24])[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:26][NH:25][C:23](=[O:24])[C:22]1[CH:27]=[CH:28][CH:29]=[C:20]([O:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:21]=1

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 6074883-Phenoxybenzhydrazide

Product 1

HCID 178517199HCID 178517199, compoundYield 83%

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-2,3-dione in acetic acid was added 3-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 403 mg of the title compound (83%) as a yellow solid in 99.5% purity by HPLC (Rt: 6.58, gradient of 10 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-ef8ce5018fc64b328adf2d715c82d8c5
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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