Diisopropylaniline → 2-[2,6-Di(propan-2-yl)phenyl]-5-nitro-1H-isoindole-1,3(2H)-dione

HRID 1058083Notes

Reaction equation

HRID 1058083 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:13]([OH:15])=O)[C:7](=[CH:11][CH:12]=1)[C:8]([OH:10])=O)([O-:3])=[O:2].[CH:16]([C:19]1[CH:25]=[CH:24][CH:23]=[C:22]([CH:26]([CH3:28])[CH3:27])[C:20]=1[NH2:21])([CH3:18])[CH3:17]>C(OCC)(=O)C>[CH:26]([C:22]1[CH:23]=[CH:24][CH:25]=[C:19]([CH:16]([CH3:18])[CH3:17])[C:20]=1[N:21]1[C:8](=[O:10])[C:7]2=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[C:6]2[C:13]1=[O:15])([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 32484DiisopropylanilineHCID 691211,2-Benzenedicarboxylic acid, 4-nitro-

Product 1

HCID 137848352-[2,6-Di(propan-2-yl)phenyl]-5-nitro-1H-isoindole-1,3(2H)-dioneYield 50%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

0.386 g of anhydride obtained by dehydrating 4-nitrophthalic acid (including 20% of 3-nitrophthalic acid) at a temperature of about 190° C., and 0.354 g of 2,6-diisopropylaniline were mixed, and reacted at a temperature of 180° C. for 4 hours. After the reaction was finished, the reaction mixture was dissolved in ethyl acetate, dried over anhydrous magnesium sulfate and subjected to filtration. The filtrate was concentrated and dried and solidified. Then, it was recrystallized by using a mixture of hexane and ethanol, to obtain 0.352 g (yield 50%) of the specified compound.

Workup

  1. additionwere mixed
  2. customreacted at a temperature of 180° C. for 4 hours
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationsubjected to filtration
  5. concentrationThe filtrate was concentrated
  6. customdried
  7. customThen, it was recrystallized
  8. additiona mixture of hexane and ethanol

Sources & evidence

ORD record
ord-ecfac2b319f64097a7b6f1ea70497d0d
Source dataset
uspto-grants-2003_02
Patent number
US06515129B1

Reaction notes

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