5-Iodoisatin → HCID 178520433, compound

HRID 642030Notes

Reaction equation

HRID 642030 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:33])[CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:19][CH:18]=1)=[O:16])[NH2:14]>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:14][NH:13][C:15]([C:17]1[CH:18]=[CH:19][C:20]([NH:23][C:24](=[O:33])[CH2:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:21][CH:22]=1)=[O:16]

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 9835476HCID 9835476, compound2×

Product 1

HCID 178520433HCID 178520433, compoundYield 77%

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-phenylpropanamide (compound B). 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 360 mg of the title compound (77%) as a yellow powder in 99.4% purity by HPLC (Rt: 4.68, 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-189d78e1e0fb44c497214be799d785be
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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