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

HRID 2301921Notes

Reaction equation

HRID 2301921 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-4efcf35f8b0e468c8f471a910bbff6b4
Source dataset
uspto-grants-2002_08
Patent number
US06429212B1

Reaction notes

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