Phthalic Anhydride → 2-(1H-Indazol-3-yl)-1H-isoindole-1,3(2H)-dione

HRID 2063583Notes

Reaction equation

HRID 2063583 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([NH2:10])=[N:2]1.[C:11]1(=O)[O:16][C:14](=[O:15])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12>O1CCOCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([N:10]2[C:14](=[O:15])[C:13]3[C:12](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:11]2=[O:16])=[N:2]1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 133991H-indazol-3-amine

Product 1

HCID 27558572-(1H-Indazol-3-yl)-1H-isoindole-1,3(2H)-dioneYield 398.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 1,4-dioxane (0.5 L) solution of 1H-indazol-3-amine (3.3 g) and phthalic anhydride (14.8 g) was stirred with heating under reflux for 15 hours. After cooled to room temperature, the reaction solution was evaporated under reduced pressure, water (50 mL) was added to the residue, and the precipitated solid was collected through filtration, washed with distilled water and ethyl acetate in that order, and dried to give the title compound as a white solid (26.0 g).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 15 hours
  3. customthe reaction solution was evaporated under reduced pressure, water (50 mL)
  4. additionwas added to the residue
  5. filtrationthe precipitated solid was collected through filtration
  6. washwashed with distilled water and ethyl acetate in that order
  7. customdried

Sources & evidence

ORD record
ord-c592c5b97d8a488fbc172f848565a9ba
Source dataset
uspto-grants-2012_10
Patent number
US08288396B2

Reaction notes

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