5-Bromoisatin → HCID 178520416, compound

HRID 642152

Reaction equation

HRID 642152 reaction equation
[Br: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.[O:13]1[C:17]2[CH:18]=[CH:19][C:20]([CH2:22][CH2:23][C:24]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]([NH:35][NH2:36])=[O:34])=[CH:29][CH:28]=3)=[O:25])=[CH:21][C:16]=2[O:15][CH2:14]1>C(O)(=O)C>[O:13]1[C:17]2[CH:18]=[CH:19][C:20]([CH2:22][CH2:23][C:24]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]([NH:35][N:36]=[C:5]4[C:4]5[C:8](=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=5)[NH:7][C:6]4=[O:11])=[O:34])=[CH:29][CH:28]=3)=[O:25])=[CH:21][C:16]=2[O:15][CH2:14]1

Participants

4

Reactant 2

HCID 68895-BromoisatinHCID 98585743-(1,3-benzodioxol-5-yl)-N-[4-(hydrazinocarbonyl)phenyl]propanamide

Product 1

HCID 178520416HCID 178520416, compoundYield 89%

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-bromo-1H-indole-2,3dione in acetic acid was added 3-(1,3-benzodioxol-5-yl)-N-[4-(hydrazinocarbonyl)phenyl]propanamide. 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 151 mg of the title compound (89%) as a yellow solid in 98.2% purity by HPLC (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-af03b36a98774c9bb50e52f2dfc83226
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Linked notes

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