5-Iodoisatin → N'-(5-iodo-2-oxoindol-3-yl)-4-phenylmethoxybenzohydrazide

HRID 642087Notes

Reaction equation

HRID 642087 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.[CH2:13]([O:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([NH:27][NH2:28])=[O:26])=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)(=O)C>[CH2:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([NH:27][N:28]=[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:26])=[CH:29][CH:30]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 15264864-(Benzyloxy)benzohydrazide

Product 1

HCID 178517213N'-(5-iodo-2-oxoindol-3-yl)-4-phenylmethoxybenzohydrazideYield 90%

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-(benzyloxy)benzohydrazide. 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 247 mg of the title compound (90%) as a yellow powder in 98.9% purity by HPLC (Rt: 5.03, gradient of 8 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-4ac2bfe14ab447cf96062ddea5992962
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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