3-Chlorophthalic anhydride → 4-Chloro-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

HRID 1162188Notes

Reaction equation

HRID 1162188 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:4]2[C:5]([O:7][C:8](=[O:9])[C:3]=12)=O.Cl.[NH2:14][CH:15]1[CH2:20][CH2:19][C:18](=[O:21])[NH:17][C:16]1=[O:22].C([O-])(=O)C.[Na+]>C(O)(=O)C>[O:22]=[C:16]1[CH:15]([N:14]2[C:8](=[O:9])[C:3]3[C:4](=[CH:10][CH:11]=[CH:12][C:2]=3[Cl:1])[C:5]2=[O:7])[CH2:20][CH2:19][C:18](=[O:21])[NH:17]1

Participants

5

Reactant 3

HCID 670143-Chlorophthalic anhydrideHCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 99480204-Chloro-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-(2,6-Dioxo(3-piperidyl))-4-chloroisoindoline-1,3-dione was prepared by the procedure of Example 1 from 3-chlorophthalic anhydride (0.40 g, 2.2 mmol), 3-aminopiperidine-2,6-dione hydrogen chloride (0.36 g, 2.2 mmol) and sodium acetate (0.19 g, 2.4 mmol) in acetic acid (10 mL). The product was a white solid (0.44 g, 69% yield); mp, 290.0-291.5° C.; 1H NMR (DMSO-d6) δ 2.05-2.11 (m, 1H, CHH), 2.49-2.64 (m, 2H, CH2), 2.64-2.92 (m, 1H, CHH), 5.17 (dd, J=5.2, 12.7 Hz, 1H, NCH), 7.86-7.94 (m, 3H, Ar), 11.17 (br s, 1H, NH); 13C NMR (DMSO-d6) δ 21.83, 30.91, 49.12, 122.41, 126.94, 129.84, 133.52, 136.11, 136.39, 164.77, 165.76, 169.73, 172.77; Anal Calcd for C13H9N2O4Cl: C, 53.35; H, 3.10; N, 9.57; Cl, 12.11. Found: C, 53.37; H, 2.94; N, 9.30, Cl, 11.97.

Sources & evidence

ORD record
ord-275db9bee4b84f638e57b11367f152f8
Source dataset
uspto-grants-2010_10
Patent number
US07820697B2

Reaction notes

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