Maleimide → 1,3,3a,4,7,7a-hexahydro-4-(2-nitrophenyl)-1,3-dioxo-7-phenyl-2H-isoindole

HRID 1165796Notes

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]/[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O-:3])=[O:2].[C:20]1(=[O:26])[NH:24][C:23](=[O:25])[CH:22]=[CH:21]1>C1(C)C=CC=CC=1.ClCCl>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[CH:11]=[CH:12][CH:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:22]2[CH:21]1[C:20](=[O:26])[NH:24][C:23]2=[O:25])([O-:3])=[O:2]

Participants

Conditions

Temperature: 130 °C

Procedure

7.5 g (29.8 mmole) (E,E)-1-(2-nitrophenyl)-4-phenyl-1,3-butadiene and 2.9 g (29.9 mmole) maleic acid imide are heated in 10 ml toluene to 130° C. for 12 hours. After addition of 1.5 g (15.5 mmole) maleic acid imide it is heated at 130° C. for a further 24 hours. After cooling, it is diluted with 40 ml dichloromethane, the product filtered off, and crystallized from ethanol. One obtains 1,3,3a,4,7,7a-hexahydro-4-(2-nitrophenyl)-1,3-dioxo-7-phenyl-2H-isoindole in the form of pale yellow crystals, which decompose from 200°-208° C.

Workup

temperatureAfter cooling
filtrationthe product filtered off
customcrystallized from ethanol

Sources & evidence

ORD record: ord-6485574def09417fb1602cf1b1443420
Source dataset: uspto-grants-1990_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04912107

Reaction notes

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