Toluene → N-benzyl-3-methyl-6-(2-nitrophenyl)-1,2,3,6-tetrahydrophthalimide

HRID 374004Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]=[CH:11][CH:12]=[CH:13][CH3:14])([O-:3])=[O:2].[C:15]1(=[O:21])[O:20][C:18](=O)[CH:17]=[CH:16]1.C1(C)C=CC=CC=1.[CH2:29]([NH2:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O.C(OCC)(=O)C>[CH2:29]([N:36]1[C:15](=[O:21])[CH:16]2[CH:13]([CH3:14])[CH:12]=[CH:11][CH:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N+:1]([O-:3])=[O:2])[CH:17]2[C:18]1=[O:20])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 5.0 g of 1-nitro-2-(1,3-pentadienyl)benzene and 2.9 g of maleic anhydride was stirred at 150° C. for 5 hours. Thereto were added 150 ml of toluene and 3.2 ml of benzylamine. The resulting mixture was azeotropically refluxed for 2 hours, and then cooled to room temperature. Thereto were added 150 ml of ethyl acetate and 100 ml of water. The organic layer was separated 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=1/0 to 20/1) to obtain 3.0 g (yield: 30%) of N-benzyl-3-methyl-6-(2-nitrophenyl)-1,2,3,6-tetrahydrophthalimide as colorless crystals.

Workup

temperatureThe resulting mixture was azeotropically refluxed for 2 hours
temperaturecooled to room temperature
customThe organic layer was separated
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was removed by distillation under reduced pressure
customThe residue was purified by column chromatography (eluant: toluene/ethyl acetate=1/0 to 20/1)

Sources & evidence

ORD record: ord-24cbd7a0d9584aadbe7036a74c311a9c
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05166204

Reaction notes

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