Phthalic Anhydride → 2-(2-methyl-4-nitrophenyl)isoindole-1,3-dione

HRID 484801Notes

Reaction equation

HRID 484801 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:12]1(=O)[O:17][C:15](=[O:16])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12>>[CH3:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[N:4]1[C:15](=[O:16])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]2[C:12]1=[O:17]

Participants

3

Reactant 2

HCID 6811Phthalic AnhydrideHCID 74412-Methyl-4-nitroaniline

Product 1

HCID 28440622-(2-methyl-4-nitrophenyl)isoindole-1,3-dioneYield 83%

Procedure

A mixture of 10.0 g (65.7 mmole) of 2-methyl-4-nitroaniline and 10.7 g (72.3 mmole) of phthalic anhydride was heated in an oil bath with an initial temperature of 150°. As the temperature was raised slowly to 165°, the mixture melted and resolidified. The cooled mixture was triturated with 200 ml of dichloromethane and filtered, and the filtrate was washed successively with 3N aqueous hydrochloric acid, water, and 5% aqueous sodium hydroxide. The organic phase was dried over calcium chloride, treated with activated charcoal, filtered, and the filtrate concentrated in vacuo. The resultant solid was suspended in hot ethanol and, after cooling, was collected and dried, giving 15.4 g of N-(2-methyl-4-nitrophenyl)phthalimide. A portion (10.0 g) of the intermediate was hydrogenated in tetrahydrofuran containing 4 ml of concentrated aqueous hydrochloric acid using 5 psi hydrogen gas over 5% palladium on carbon. The filtered solution was concentrated to dryness and the resultant solid washed with methanol, giving 8.3 g of the title compound. The product thus isolated was used in subsequent reactions without further purification.

Workup

  1. temperaturewas heated in an oil bath with an initial temperature of 150°
  2. temperatureAs the temperature was raised slowly to 165°
  3. customThe cooled mixture was triturated with 200 ml of dichloromethane
  4. filtrationfiltered
  5. washthe filtrate was washed successively with 3N aqueous hydrochloric acid, water, and 5% aqueous sodium hydroxide
  6. dry with materialThe organic phase was dried over calcium chloride
  7. additiontreated with activated charcoal
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated in vacuo
  10. temperatureafter cooling
  11. customwas collected
  12. customdried

Sources & evidence

ORD record
ord-93a0744065784496b79daddb23fa6658
Source dataset
uspto-grants-1985_08
Patent number
US04533739

Reaction notes

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