Triethylamine → 2-(2,4-Dinitrophenoxy)-1H-isoindole-1,3(2H)-dione

HRID 876811Notes

Reaction equation

HRID 876811 reaction equation
[OH:1][N:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12].CCN(CC)CC.Br[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:22]=1[N+:30]([O-:32])=[O:31]>CC(C)=O>[N+:27]([C:24]1[CH:23]=[C:22]([N+:30]([O-:32])=[O:31])[CH:21]=[CH:26][C:25]=1[O:1][N:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12])([O-:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 114411-Bromo-2,4-dinitrobenzene

Product 1

HCID 70363092-(2,4-Dinitrophenoxy)-1H-isoindole-1,3(2H)-dioneYield 96.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 2-hydroxyisoindoline-1,3-dione (20.0 g, 0.12 mol) in acetone (400 mL) was added Et3N (14.9 g, 0.15 mol), the mixture was stirred at room temperature until it became a homogeneous solution, then 1-bromo-2,4-dinitrobenzene Y-1 (30.2 g, 0.12 mol) was added. The reaction was stirred at room temperature for 3 h, then poured into ice-water, the resulting precipitate was filtered and washed three times with cold MeOH, dried in vacuum to afford the title compound (38.1 g).

Workup

  1. stirringThe reaction was stirred at room temperature for 3 h
  2. filtrationthe resulting precipitate was filtered
  3. washwashed three times with cold MeOH
  4. customdried in vacuum

Sources & evidence

ORD record
ord-dbb3f970c0724ff3a7a479fecd60add1
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

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