Phthalic Anhydride → 2-(1,3-Isoindolinedion-2-yl)indane

HRID 1598558Notes

Reaction equation

HRID 1598558 reaction equation
[NH2:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]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>C(O)(=O)C>[C:11]1(=[O:16])[C:12]2[C:13](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:14](=[O:15])[N:1]1[CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 763102-Aminoindane

Product 1

HCID 109998862-(1,3-Isoindolinedion-2-yl)indaneYield 86.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 200 ml of acetic acid were added 26.4 g of 2-amino-indane and 44.5 g of phthalic anhydride, and the mixture was refluxed under heating for 17 hours. The reaction mixture was poured into ice water, and crystals precipitated were collected by filtration, washed, dried and then recrystallized from ethyl acetate to obtain 45.04 g of 2-(1,3-isoindolinedion-2-yl)indane.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 17 hours
  3. customprecipitated
  4. filtrationwere collected by filtration
  5. washwashed
  6. customdried
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-0f525eee504e4e0f8f06a88f4df6d2e3
Source dataset
uspto-grants-1998_04
Patent number
US05739132

Reaction notes

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