5-Iodoisatin → HCID 178521267, compound

HRID 642079Notes

Reaction equation

HRID 642079 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]1([C:18]2[N:19]=[N:20][N:21]([CH2:23][C:24]([NH:26][NH2:27])=[O:25])[N:22]=2)[CH2:17][CH2:16][CH2:15][CH2:14]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:27][NH:26][C:24](=[O:25])[CH2:23][N:21]1[N:20]=[N:19][C:18]([N:13]2[CH2:14][CH2:15][CH2:16][CH2:17]2)=[N:22]1

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 2730063HCID 2730063, compound

Product 1

HCID 178521267HCID 178521267, compoundYield 72%

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-(1-pyrrolidinyl)-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 67 mg of the title compound (72%) as a yellow powder in 95% purity by HPLC (Rt: 4.24, 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-d27febe73ab148c2bc9343c9d095a823
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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