p-Phenylbenzhydrazide → N'-(5-iodo-2-oxoindol-3-yl)-4-phenylbenzohydrazide

HRID 642039Notes

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]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:18]=[CH:17][C:16]([C:19]([NH:21][NH2:22])=[O:20])=[CH:15][CH:14]=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:22][NH:21][C:19]([C:16]1[CH:17]=[CH:18][C:13]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:14][CH:15]=1)=[O:20]

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 (1,1′-biphenyl)-4-carbohydrazide. 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 201 mg of the title compound (86%) as a yellow solid in 99.8% purity by HPLC (Rt: 6.49, 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-af79eee4a2cf42efbe2279eb192ef061
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696231B2

Reaction notes

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