Homophthalic anhydride → 1,3(2H,4H)-Isoquinolinedione, 2-[2,6-bis(1-methylethyl)phenyl]-

HRID 1058086Notes

Reaction equation

HRID 1058086 reaction equation
[C:1]1(=[O:12])[O:7][C:5](=O)[C:4]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:3]2[CH2:2]1.[CH:13]([C:16]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]([CH3:25])[CH3:24])[C:17]=1[NH2:18])([CH3:15])[CH3:14]>C(OCC)(=O)C>[CH:23]([C:19]1[CH:20]=[CH:21][CH:22]=[C:16]([CH:13]([CH3:15])[CH3:14])[C:17]=1[N:18]1[C:5](=[O:7])[C:4]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:3]2[CH2:2][C:1]1=[O:12])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 12801Homophthalic anhydrideHCID 32484Diisopropylaniline

Product 1

HCID 98619241,3(2H,4H)-Isoquinolinedione, 2-[2,6-bis(1-methylethyl)phenyl]-Yield 36%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

0.512 g (3.16 mmol) of homophthalic anhydride and 0.42 g (2.37 mmol) of 2,6-diisopropylaniline were mixed, and melted at a temperature of 200° C. for 1 hour. The reactant was dissolved in ethyl acetate, washed with aqueous NaHCO3 solution, with water and then with saturated aqueous sodium chloride, dried over anhydrous MgSO4, and subjected to filtration with a folded filter paper. The filtrate was concentrated and evaporated to dryness. The residue was recrystallized by using a mixture of CH2Cl2 and hexane, to obtain 0.351 g (yield 36%) of the specified substance as light purple leaflets. It showed the following physical properties and analyzed values.

Workup

  1. washwashed with aqueous NaHCO3 solution, with water
  2. dry with materialwith saturated aqueous sodium chloride, dried over anhydrous MgSO4
  3. filtrationsubjected to filtration with a folded filter paper
  4. concentrationThe filtrate was concentrated
  5. customevaporated to dryness
  6. customThe residue was recrystallized
  7. additiona mixture of CH2Cl2 and hexane
  8. customto obtain 0.351 g (yield 36%) of the specified substance as light purple leaflets

Sources & evidence

ORD record
ord-b9204e724e76417d95102aec06b50d6e
Source dataset
uspto-grants-2003_02
Patent number
US06515129B1

Reaction notes

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