5-Iodoisatin → HCID 178497969, compound

HRID 642106Notes

Reaction equation

HRID 642106 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.[NH:13]([C:15](=[O:28])[CH2:16][O:17][C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=1)[C:21]([O:23][CH3:24])=[O:22])[NH2:14]>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:14][NH:13][C:15](=[O:28])[CH2:16][O:17][C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=1)[C:21]([O:23][CH3:24])=[O:22]

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 9964555HCID 9964555, compound

Product 1

HCID 178497969HCID 178497969, compoundYield 79%

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 methyl 3-(2-hydrazino-2-oxoethoxy)benzoate. 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 380 mg of the title compound (79%) as a orange powder in 98.9% purity by HPLC (Rt: 4.3, 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-143cd9b3a1e74ae799707a5347cc66c4
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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