5-Iodoisatin → HCID 178517217, compound

HRID 642097Notes

Reaction equation

HRID 642097 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]([N:21]1[CH2:26][CH2:25][CH:24]([C:27]([NH:29][NH2:30])=[O:28])[CH2:23][CH2:22]1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)(=O)C>[C:13]([N:21]1[CH2:26][CH2:25][CH:24]([C:27]([NH:29][N:30]=[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:28])[CH2:23][CH2:22]1)(=[O:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 99648491-Benzoylpiperidine-4-carbohydrazide

Product 1

HCID 178517217HCID 178517217, compoundYield 88%

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 (±)-1-benzoyl-4-piperidinecarbohydrazide. 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 221 mg of the title compound (88%) as a yellow solid in 94.1% purity by HPLC (Rt: 3.93, 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-88232294784047688835f8ab41535cc7
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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