m-Anisohydrazide → HCID 178490564, compound

HRID 642043Notes

Reaction equation

HRID 642043 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.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=1)[C:18]([NH:20][NH2:21])=[O:19]>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:21][NH:20][C:18](=[O:19])[C:17]1[CH:22]=[CH:23][CH:24]=[C:15]([O:14][CH3:13])[CH:16]=1

Participants

4

Reactant 2

HCID 79848m-AnisohydrazideHCID 886955-Iodoisatin

Product 1

HCID 178490564HCID 178490564, compoundYield 82%

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 3-methoxybenzohydrazide. 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 345 mg of the title compound (82%) as a yellow solid in 99.7% purity by HPLC (Rt: 5.5, gradient of 10 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-63022755d650403d8a47ae01af29a786
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

Loading…