5-Iodoisatin → HCID 178517209, compound

HRID 642049Notes

Reaction equation

HRID 642049 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[O:20][C:19]([C:21]([NH:23][NH2:24])=[O:22])=[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:24][NH:23][C:21]([C:19]1[O:20][C:16]([N+:13]([O-:15])=[O:14])=[CH:17][CH:18]=1)=[O:22]

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 37135982-Furancarboxylic acid, 5-nitro-, hydrazide

Product 1

HCID 178517209HCID 178517209, compoundYield 74%

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 5-nitro-2-furohydrazide. 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 158 mg of the title compound (74%) as a Orange solid in 98.3% purity by HPLC (Rt: 5.31, 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-e310eb2708ed45f4b0658ddefdc67cb6
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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