Triphenylphosphine → N-benzyl-2-methylcarbazole-3,4-dicarboximide

HRID 374006Notes

Reaction equation

HRID 374006 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[C:11]2=[C:14]([CH3:27])[CH:15]=[CH:16][C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N+:24]([O-])=O)=[C:10]2[C:9]1=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClC1C=CC=CC=1Cl>[CH2:1]([N:8]1[C:9](=[O:28])[C:10]2[C:17]3[C:18]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[NH:24][C:16]=3[CH:15]=[C:14]([CH3:27])[C:11]=2[C:12]1=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 19808742N-benzyl-3-methyl-6-(2-nitrophenyl)phthalimide

Product 1

HCID 19808782N-benzyl-2-methylcarbazole-3,4-dicarboximideYield 47%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

30 ml of o-dichlorobenzene was added to a mixture of 2.0 g of N-benzyl-3-methyl-6-(2-nitrophenyl)-phthalimide and 4.2 g of triphenylphosphine. The mixture was refluxed for 8 hours. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: toluene/ethyl acetate=50/1), followed by recrystallization from n-propanol to obtain 850 mg (yield: 47%) of N-benzyl-2-methylcarbazole-3,4-dicarboximide as yellow crystals.

Workup

  1. temperatureThe mixture was refluxed for 8 hours
  2. customThe solvent was removed by distillation under reduced pressure
  3. customThe residue was purified by column chromatography (eluant: toluene/ethyl acetate=50/1)
  4. customfollowed by recrystallization from n-propanol

Sources & evidence

ORD record
ord-b2a4bfbfe4304a2db3bc25627cf1f251
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

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