3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione → 1-Oxo-2-(2,6-dioxopiperidin-3-yl)-6-nitroisoindoline

HRID 651434Notes

Reaction equation

HRID 651434 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[CH2:4][N:3]1[CH:14]1[CH2:19][CH2:18][C:17](=[O:20])[NH:16][C:15]1=[O:21].[O:22]=[C:23]1[C:31]2[C:26](=[C:27]([N+:32]([O-:34])=[O:33])[CH:28]=[CH:29][CH:30]=2)[CH2:25][N:24]1[CH:35]1[CH2:40][CH2:39][C:38](=[O:41])[NH:37][C:36]1=[O:42]>>[O:22]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=2)[CH2:2][N:3]1[CH:14]1[CH2:19][CH2:18][C:17](=[O:20])[NH:16][C:15]1=[O:21].[O:1]=[C:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][C:27]=2[N+:32]([O-:34])=[O:33])[CH2:23][N:24]1[CH:35]1[CH2:40][CH2:39][C:38](=[O:41])[NH:37][C:36]1=[O:42]

Participants

4

Reactant 2

HCID 114717813-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dioneHCID 219282773-(5-Nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Product 2

HCID 219282651-Oxo-2-(2,6-dioxopiperidin-3-yl)-6-nitroisoindolineHCID 219282731-Oxo-2-(2,6-dioxopiperidine-3-yl)-7-nitroisoindoline

Procedure

1-Oxo-2-(2,6-dioxopiperidin-3-yl)-5-nitroisoindoline, 1-oxo-2-(2,6-dioxopiperidin-3-yl )-4-nitroisoindoline. 1-oxo-2-(2,6-dioxopiperidin-3-yl)-6-nitroisoindoline, and 1-oxo-2-(2,6-dioxopiperidine-3-yl)-7-nitroisoindoline can be obtained by allowing 2,6-dioxopiperidin-3-ammonium chloride to react with methyl 2-bromomethyl-5-nitrobenzoate, methyl 2-bromomethyl-4-nitrobenzoate methyl 2-bromomethyl-6-nitrobenzoate, and methyl 2-bromomethyl-7-nitrobenzoate, respectively, in dimethylformamide in the presence of triethylamine. The methyl 2-(bromomethyl)nitrobenzoates in turn are obtained from the corresponding methyl esters of nitro-orthotoluic acids by conventional bromination with N-bromosuccinimide under the influence of light.

Sources & evidence

ORD record
ord-95a0ff761e034287a423649da67bdc38
Source dataset
uspto-grants-2001_08
Patent number
US06281230B1

Reaction notes

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