5-Iodoisatin → HCID 178521266, compound

HRID 642078Notes

Reaction equation

HRID 642078 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.[N+:13]([C:16]1[CH:17]=[C:18]([C:22]2[N:23]=[N:24][N:25]([CH2:27][C:28]([NH:30][NH2:31])=[O:29])[N:26]=2)[CH:19]=[CH:20][CH:21]=1)([O-:15])=[O:14]>C(O)(=O)C>[N+:13]([C:16]1[CH:17]=[C:18]([C:22]2[N:23]=[N:24][N:25]([CH2:27][C:28]([NH:30][N:31]=[C:5]3[C:4]4[C:8](=[CH:9][CH:10]=[C:2]([I:1])[CH:3]=4)[NH:7][C:6]3=[O:11])=[O:29])[N:26]=2)[CH:19]=[CH:20][CH:21]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 2730590HCID 2730590, compound

Product 1

HCID 178521266HCID 178521266, compoundYield 77%

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 2-[5-(3-nitrophenyl)-2H-tetrazol-2-yl]acetohydrazide. 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 80 mg of the title compound (77%) as a yellow powder in 97% purity by HPLC (Rt: 4.96, gradient of 8 min, MaxPlot detection between 230 and 400 nm).

Workup

  1. temperaturewas 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-ecc61742e9864beb8c126ae2513aa8ab
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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