5-Iodoisatin → HCID 178497995, compound

HRID 642061Notes

Reaction equation

HRID 642061 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]([C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][N:18]=1)=[O:16])[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]([C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][N:18]=1)=[O:16]

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 2801744HCID 2801744, compound

Product 1

HCID 178497995HCID 178497995, compoundYield 73%

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 6-(hydrazinocarbonyl)nicotinate. 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 33 mg of the title compound (73%) as a yellow solid in 89.7% purity by HPLC (Rt: 4.44, 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-4ca403c539ae4d52b490b2e60b1e0db6
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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