3-Aminopiperidine-2,6-dione hydrochloride → 2-(2,6-Dioxopiperidin-3-yl)-5-nitro-1H-isoindole-1,3(2H)-dione

HRID 1843447Notes

Reaction equation

HRID 1843447 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[O:10][C:8](=O)[C:7]2=[CH:13][CH:14]=1)([O-:3])=[O:2].[CH2:15]1[CH:22]([NH2:23])[C:20](=[O:21])[NH:19][C:17](=[O:18])[CH2:16]1.Cl>C(O)(=O)C.C([O-])(=O)C.[Na+]>[O:10]=[C:8]1[C:7]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:14][CH:13]=2)[C:11](=[O:12])[N:23]1[CH:22]1[CH2:15][CH2:16][C:17](=[O:18])[NH:19][C:20]1=[O:21]

Participants

5

Reactant 2

HCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 2309764-Nitrophthalic acid anhydride

Product 1

HCID 155520312-(2,6-Dioxopiperidin-3-yl)-5-nitro-1H-isoindole-1,3(2H)-dioneYield 54%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 517045Sodium AcetateSolvent

Procedure

The same patents also describe the preparation of the nitro intermediate. 4-Nitro-phthalic anhydride is coupled with 2,6-dioxopiperidine-3-ammonium chloride in glacial acetic acid and sodium acetate to obtain 1,3-dioxo-2-(2,6-dioxopiperidin-3-yl)-5-nitro-isoindoline in 54% yield. The preparation of the nitro intermediate 3-(1-oxo-4-nitro-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione follows the same reaction conditions as described, resulting in a low yield of the nitro intermediate of about 55%.

Sources & evidence

ORD record
ord-14732a5fcb1848a697d9ee3453f52a0c
Source dataset
uspto-grants-2015_02
Patent number
US08946265B2

Reaction notes

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