p-Toluohydrazide → HCID 178425870, compound

HRID 642033Notes

Reaction equation

HRID 642033 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.[CH3:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([NH:20][NH2:21])=[O:19])=[CH:16][CH:15]=1>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:21][NH:20][C:18](=[O:19])[C:17]1[CH:22]=[CH:23][C:14]([CH3:13])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 77174p-ToluohydrazideHCID 886955-Iodoisatin

Product 1

HCID 178425870HCID 178425870, compoundYield 80%

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 4-methylbenzohydrazide. 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 163 mg of the title compound (80%) as a yellow solid in 99.99% purity by HPLC (Rt: 5.7, 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-829fab3672dd4a01b963fe2dbe5bd1f0
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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