5-Iodoisatin → HCID 178520465, compound

HRID 642118Notes

Reaction equation

HRID 642118 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.[NH:13]([C:15]([C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:34])[CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([OH:33])[CH:28]=2)=[CH:19][CH:18]=1)=[O:16])[NH2:14]>C(O)(=O)C>[OH:33][C:29]1[CH:28]=[C:27]([CH2:26][CH2:25][C:24]([NH:23][C:20]2[CH:21]=[CH:22][C:17]([C:15]([NH:13][N:14]=[C:5]3[C:4]4[C:8](=[CH:9][CH:10]=[C:2]([I:1])[CH:3]=4)[NH:7][C:6]3=[O:11])=[O:16])=[CH:18][CH:19]=2)=[O:34])[CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 68409551HCID 68409551, compound

Product 1

HCID 178520465HCID 178520465, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Into a suspension of 5-iodo-1H-indole-2,3-dione in acetic acid was added N-[4-(hydrazinocarbonyl)phenyl]-3-(3-hydroxyphenyl)propanamide. 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 45 mg of the title compound (63%) as a yellow solid in 92.4% purity by HPLC (Rt: 3.88, 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-3e5168a30021491788180762b8c34fc1
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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