5-Iodoisatin → HCID 178520488, compound

HRID 642116Notes

Reaction equation

HRID 642116 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.[OH:13][C:14]1[CH:15]=[C:16]([CH2:21][CH2:22][C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([NH:34][NH2:35])=[O:33])=[CH:28][CH:27]=2)=[O:24])[CH:17]=[CH:18][C:19]=1[OH:20]>C(O)(=O)C>[OH:13][C:14]1[CH:15]=[C:16]([CH2:21][CH2:22][C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([NH:34][N:35]=[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:33])=[CH:28][CH:27]=2)=[O:24])[CH:17]=[CH:18][C:19]=1[OH:20]

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 9879898HCID 9879898, compound

Product 1

HCID 178520488HCID 178520488, compoundYield 87%

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 3-(3,4-dihydroxyphenyl)-N-[4-(hydrazinocarbonyl)phenyl]propanamide. 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 161 mg of the title compound (87%) as a yellow solid in 96% purity by HPLC (Rt: 3.56, 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-54271249a84341df9e96368ac2b6d308
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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