2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → N-benzyl-3-methyl-6-(2-nitrophenyl)phthalimide

HRID 374005Notes

Reaction equation

HRID 374005 reaction equation
ClC1C=CC=CC=1.[CH2:8]([N:15]1[C:19](=[O:20])[CH:18]2[CH:21]([CH3:34])[CH:22]=[CH:23][CH:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[N+:31]([O-:33])=[O:32])[CH:17]2[C:16]1=[O:35])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(OCC)(=O)C>[CH2:8]([N:15]1[C:19](=[O:20])[C:18]2=[C:21]([CH3:34])[CH:22]=[CH:23][C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[N+:31]([O-:33])=[O:32])=[C:17]2[C:16]1=[O:35])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 7964ChlorobenzeneHCID 19808704N-benzyl-3-methyl-6-(2-nitrophenyl)-1,2,3,6-tetrahydrophthalimide

Product 1

HCID 19808742N-benzyl-3-methyl-6-(2-nitrophenyl)phthalimideYield 40.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

30 ml of chlorobenzene was added to a mixture of 5.0 g of N-benzyl-3-methyl-6-(2-nitrophenyl)-1,2,3,6-tetrahydrophthalimide and 7.0 g of DDQ. The mixture was refluxed for 8 hours, then cooled to room temperature. Thereto was added 100 ml of ethyl acetate. The resulting mixture was washed with aqueous 10% potassium carbonate solution and an aqueous saturated sodium chloride solution in this order and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: toluene/ethyl acetate=100/1 to 80/1), followed by recrystallization from ethanol to obtain 2.0 g (yield: 40%) of N-benzyl-3-methyl-6-(2-nitrophenyl)phthalimide as light yellow crystals.

Workup

  1. temperatureThe mixture was refluxed for 8 hours
  2. washThe resulting mixture was washed with aqueous 10% potassium carbonate solution
  3. dry with materialan aqueous saturated sodium chloride solution in this order and dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customThe residue was purified by column chromatography (eluant: toluene/ethyl acetate=100/1 to 80/1)
  6. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-fe3f62a355504b488403feecb2064b33
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

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