5-Iodoisatin → HCID 178517204, compound

HRID 642031Notes

Reaction equation

HRID 642031 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.[Cl:13][C:14]1[CH:15]=[C:16]([CH:21]=[C:22]([Cl:24])[CH:23]=1)[C:17]([NH:19][NH2:20])=[O:18]>C(O)(=O)C>[Cl:13][C:14]1[CH:15]=[C:16]([CH:21]=[C:22]([Cl:24])[CH:23]=1)[C:17]([NH:19][N:20]=[C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([I:1])[CH:3]=2)[NH:7][C:6]1=[O:11])=[O:18]

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 27359663,5-dichlorobenzohydrazide

Product 1

HCID 178517204HCID 178517204, compoundYield 69%

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 3,5-dichlorobenzohydrazide. 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 159 mg of the title compound (69%) as a orange solid in 90% purity by HPLC (Rt: 5.86, 6.66, 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-03a0942cf4c54ad88fb2a2703917dd6c
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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