5-Iodoisatin → HCID 178517223, compound

HRID 642134Notes

Reaction equation

HRID 642134 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]([S:15]([C:18]1[CH:19]=[CH:20][C:21]([OH:27])=[C:22]([CH:26]=1)[C:23]([OH:25])=[O:24])(=[O:17])=[O:16])[NH2:14]>C(O)(=O)C>[OH:27][C:21]1[CH:20]=[CH:19][C:18]([S:15]([NH:13][N:14]=[C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([I:1])[CH:3]=3)[NH:7][C:6]2=[O:11])(=[O:16])=[O:17])=[CH:26][C:22]=1[C:23]([OH:25])=[O:24]

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 4408837HCID 4408837, compound

Product 1

HCID 178517223HCID 178517223, compoundYield 59%

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-(hydrazinosulfonyl)-2-hydroxybenzoic acid. 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 108 mg of the title compound (59%) as a yellow solid in 92.8% purity by HPLC (Rt: 4.85, gradient of 10 min, MaxPlot detection between 230 and 400 mn).

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-5518c01644c647eea95285d849a3cc70
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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