5-Iodoisatin → HCID 178517196, compound

HRID 642102Notes

Reaction equation

HRID 642102 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:35]=[CH:34][C:20]([CH2:21][NH:22][C:23](=[O:33])[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[CH:25]=2)=[CH:19][CH:18]=1)=[O:16])[NH2:14]>C(O)(=O)C>[N+:30]([C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=1)[C:23]([NH:22][CH2:21][C:20]1[CH:19]=[CH:18][C:17]([C:15]([NH:13][N:14]=[C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([I:1])[CH:3]=3)[NH:7][C:6]2=[O:11])=[O:16])=[CH:35][CH:34]=1)=[O:33])([O-:32])=[O:31]

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 9966612HCID 9966612, compound

Product 1

HCID 178517196HCID 178517196, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Into a suspension of 5-iodo-1H-indole-2,3-dione in acetic acid was added N-[4-(hydrazinocarbonyl)benzyl]-3-nitrobenzamide. 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 252 mg of the title compound (89%) as a orange solid in 95.4% purity by HPLC (Rt: 4.15, 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-0cfbb519671d40eeab4d2462bad831d5
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

Loading…