5-Bromoisatin → HCID 178517025, compound

HRID 642132Notes

Reaction equation

HRID 642132 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.[NH:13]1[C:17]([C:18]2[CH:27]=[CH:26][C:21]([C:22]([NH:24][NH2:25])=[O:23])=[CH:20][CH:19]=2)=[N:16][N:15]=[N:14]1>C(O)(=O)C>[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=[N:25][NH:24][C:22](=[O:23])[C:21]1[CH:26]=[CH:27][C:18]([C:17]2[NH:16][N:15]=[N:14][N:13]=2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 68895-BromoisatinHCID 178514418HCID 178514418, compound

Product 1

HCID 178517025HCID 178517025, compoundYield 53%

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 4-(1H-tetrazol-5-yl)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 29 mg of the title compound (53%) as a orange Solid in 89.1% purity by HPLC (Rt: 3.29, 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-6538b5b5eb4f40a89512e592cbd12d68
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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