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

HRID 1058082Notes

Reaction equation

HRID 1058082 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]=1C(O)=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:29](OCC)(=[O:31])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:7](=[O:9])[C:6]2=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=[C:10]2[C:29]1=[O:31])([CH3:28])[CH3:27]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 32484DiisopropylanilineHCID 690433-Nitrophthalic acid

Product 1

HCID 137848352-[2,6-Di(propan-2-yl)phenyl]-5-nitro-1H-isoindole-1,3(2H)-dioneYield 45%

Procedure

0.386 g of anhydride obtained by dehydrating 3-nitrophthalic acid at a temperature of about 220° 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 ethyl acetate, to obtain 0.320 g (yield 45%) 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 ethyl acetate

Sources & evidence

ORD record
ord-36faf1f4419641c1b3091703320cfe01
Source dataset
uspto-grants-2003_02
Patent number
US06515129B1

Reaction notes

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