5-Iodoisatin → HCID 178509874, compound

HRID 642070Notes

Reaction equation

HRID 642070 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.[C:13]([C:15]1[CH:33]=[CH:32][C:18]([C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([NH:30][NH2:31])=[O:29])=[CH:24][CH:23]=2)=[O:20])=[CH:17][CH:16]=1)#[N:14]>C(O)(=O)C>[C:13]([C:15]1[CH:16]=[CH:17][C:18]([C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([NH:30][N:31]=[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:29])=[CH:24][CH:23]=2)=[O:20])=[CH:32][CH:33]=1)#[N:14]

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 9878803HCID 9878803, compound

Product 1

HCID 178509874HCID 178509874, compoundYield 89%

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 4-cyano-N-[4-(hydrazinocarbonyl)phenyl]benzamide. 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 95 mg of the title compound (89%) as a orange powder in 94.7% purity by HPLC (Rt: 4.37, gradient of 8 min, MaxPlot detection between 230 and 400 nm).

Workup

  1. temperaturewas 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-109537f37940477694e63ba8e4e2b9b7
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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