Ethanol → 1,3-dihydro-4-(2-nitrophenyl)-1,3-dioxo-7-phenyl-2H-isoindole

HRID 1165795Notes

Reaction equation

HRID 1165795 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[CH:18]=[CH:17][CH:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:15]2[CH:11]1[C:12](=[O:26])[NH:13][C:14]2=[O:25])([O-:3])=[O:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C(O)C>C(C1C=CC=CC=1)(C)(C)C>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:15]2[C:11]=1[C:12](=[O:26])[NH:13][C:14]2=[O:25])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 146772841,3,3a,4,7,7a-hexahydro-4-(2-nitrophenyl)-1,3-dioxo-7-phenyl-2H-isoindole

Product 1

HCID 146772851,3-dihydro-4-(2-nitrophenyl)-1,3-dioxo-7-phenyl-2H-isoindole

Reagents, catalysts & solvents 1

HCID 7366Tert-ButylbenzeneSolvent

Procedure

5.5 g (15.8 mmole) 1,3,3a,4,7,7a-hexahydro-4-(2-nitrophenyl)-1,3-dioxo-7-phenyl-2H-isoindole and 9.1 g (40.1 mmole) 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) are heated under reflux for 16 hours in 100 ml t-butylbenzene. The solvent is removed in a vacuum and the residue chromatographed on silica gel with toluene/ethyl acetate 3:1. The fraction with the Rf of 0.4 is isolated, stirred with a little hot ethanol, and the crystals formed after cooling are filtered off. After recrystallization from ethyl acetate, one obtains 1,3-dihydro-4-(2-nitrophenyl)-1,3-dioxo-7-phenyl-2H-isoindole in the form of colorless crystals of the mp 224°-226° C.

Workup

  1. customThe solvent is removed in a vacuum
  2. customthe residue chromatographed on silica gel with toluene/ethyl acetate 3:1
  3. customThe fraction with the Rf of 0.4 is isolated
  4. customthe crystals formed
  5. temperatureafter cooling
  6. filtrationare filtered off
  7. customAfter recrystallization from ethyl acetate, one

Sources & evidence

ORD record
ord-ac6d175fc7f444c19a9bffb6255a90b8
Source dataset
uspto-grants-1990_03
Patent number
US04912107

Reaction notes

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