3,6-Dimethylphthalic anhydride → 2-(2,6-Dioxopiperid-3-yl)-4,7-dimethylisoindoline-1,3-dione

HRID 1162184Notes

Reaction equation

HRID 1162184 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][C:10]([CH3:13])=[C:4]2[C:5]([O:7][C:8](=[O:9])[C:3]=12)=O.Cl.[NH2:15][CH:16]1[CH2:21][CH2:20][C:19](=[O:22])[NH:18][C:17]1=[O:23].C([O-])(=O)C.[Na+]>C(O)(=O)C>[O:23]=[C:17]1[CH:16]([N:15]2[C:5](=[O:7])[C:4]3[C:3](=[C:2]([CH3:1])[CH:12]=[CH:11][C:10]=3[CH3:13])[C:8]2=[O:9])[CH2:21][CH2:20][C:19](=[O:22])[NH:18]1

Participants

5

Reactant 3

HCID 216163,6-Dimethylphthalic anhydrideHCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 99039762-(2,6-Dioxopiperid-3-yl)-4,7-dimethylisoindoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-(2,6-Dioxopiperid-3-yl)-4,7-dimethylisoindoline-1,3-dione was prepared by the procedure of Example 1 from 3,6-dimethylphthalic anhydride (220 mg, 1.25 mmol), 3-aminopiperidine-2,6-dione hydrogen chloride (204 mg, 1.24 mmol) and sodium acetate (110 mg, 1.34 mmol) in acetic acid (10 mL). The product is a white solid (200 mg, 56% yield): mp 263.0-265.0° C.; 1H-NMR (DMSO-d6) δ 2.01-2.07 (m, 1H, CHH), 2.50-2.89 (m, 9H, CH3, CHH, CH2), 5.10 (dd, J=5.1, 12.4 Hz, 1H, NCH), 7.52 (s, 2H, Ar), 11.12 (br s, 1H, NH); 13C NMR (DMSO-d6) δ 16.82, 22.02, 30.97, 48.59, 128.01, 135.04, 136.58, 167.68, 169.98, 172.83.

Sources & evidence

ORD record
ord-87320a5fd3c94befbd73dd08317eb0e6
Source dataset
uspto-grants-2010_10
Patent number
US07820697B2

Reaction notes

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