2,6-Dimethylaniline → 1,3(2H,4H)-Isoquinolinedione, 2-(2,6-dimethylphenyl)-

HRID 2301920Notes

Reaction equation

HRID 2301920 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.[CH3:13][C:14]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:15]=1[NH2:16]>C(OCC)(=O)C>[CH3:13][C:14]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:15]=1[N:16]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]

Participants

4

Reactant 2

HCID 68962,6-DimethylanilineHCID 12801Homophthalic anhydride

Product 1

HCID 1827511,3(2H,4H)-Isoquinolinedione, 2-(2,6-dimethylphenyl)-Yield 68%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

0.67 g (4.13 mmol) of homophthalic anhydride and 0.4 g (3.30 mmol) of 2,6-dimethylaniline 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 0.565 g (yield 68%) of the specified substance as light yellow granulated crystals. 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 0.565 g (yield 68%) of the specified substance as light yellow granulated crystals

Sources & evidence

ORD record
ord-552f155c24d8450bbf5f748cf90a8017
Source dataset
uspto-grants-2002_08
Patent number
US06429212B1

Reaction notes

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