Phthalic Anhydride → 1H-Isoindole-1,3(2H)-dione, 2-(2-nitrophenyl)-

HRID 859154

Reaction equation

HRID 859154 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[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>[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[N:6]1[C:14](=[O:15])[C:13]2[C:12](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]1=[O:16])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 69462-Nitroaniline

Product 1

HCID 1013131H-Isoindole-1,3(2H)-dione, 2-(2-nitrophenyl)-Yield 121.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 2-nitroaniline (1 g, 7.23 mmol) in acetic acid (5 mL) was added phthalic anhydride (1.29 g, 8.7 mmol) followed by stirring at ambient temperature for 16 h. The mixture was then heated at reflux for 20 h. Upon cooling, a yellow precipitate formed and was collected by filtration. The filtrate was washed with acetic acid and was dried under a under a stream of air to give 2.35 g (100%) of 2-(2-nitrophenyl)isoindole-1,3-dione: 1H NMR (300 MHz, DMSO-d6) δ 8.21 (m, 1H), 8.02–7.95 (m, 5H), 7.77 (m, 2H).

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 20 h
  3. temperatureUpon cooling
  4. customa yellow precipitate formed
  5. filtrationwas collected by filtration
  6. washThe filtrate was washed with acetic acid
  7. customwas dried under a under a stream of air

Sources & evidence

ORD record
ord-cfef55bccd114a1582a70315f056a556
Source dataset
uspto-grants-2006_12
Patent number
US07151112B1

Linked notes

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