5-Iodoisatin → HCID 178521414, compound

HRID 642046Notes

Reaction equation

HRID 642046 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.[N+:13]([C:16]1[CH:27]=[CH:26][C:19]([O:20][CH2:21][C:22]([NH:24][NH2:25])=[O:23])=[CH:18][CH:17]=1)([O-:15])=[O:14]>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:25][NH:24][C:22](=[O:23])[CH2:21][O:20][C:19]1[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 156556Acetic acid, (4-nitrophenoxy)-, hydrazide

Product 1

HCID 178521414HCID 178521414, compoundYield 85%

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 2-(4-nitrophenoxy)acetohydrazide. 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 395 mg of the title compound (85%) as a yellow solid in 97.3% purity by HPLC (Rt: 5.76, 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-6951eed442934de884b7b69f4a4ff9a0
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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