5-Iodoisatin → 4-tert-butyl-N'-(5-iodo-2-oxoindol-3-yl)benzohydrazide

HRID 642038

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]([C:17]1[CH:26]=[CH:25][C:20]([C:21]([NH:23][NH2:24])=[O:22])=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14]>C(O)(=O)C>[C:13]([C:17]1[CH:26]=[CH:25][C:20]([C:21]([NH:23][N:24]=[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:22])=[CH:19][CH:18]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

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-tert-butylbenzohydrazide. 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 168 mg of the title compound (75%) as a yellow solid in 99.8% purity by HPLC (Rt: 6.65, gradient of 10 min, MaxPlot detection between 230 and 400 nm).

Workup

temperaturethe reaction mixture was cooled to rt
customa yellow solid precipitated out
filtrationFiltration on a fritté
washwashing with AcOH, water
customdrying under vacuo at 60° C. overnight

Sources & evidence

ORD record: ord-fdbfdf3024b4465e97cbdea545049adb
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696231B2

Linked notes

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