4-Methyl-1,3-isobenzofurandione → 4-Methyl-2-(2,6-dioxo-3-methyl-(3-piperidyl))isoindoline-1,3-dione

HRID 2185956Notes

Reaction equation

HRID 2185956 reaction equation
[CH3:1][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][C:15]1([CH3:23])[CH2:20][CH2:19][C:18](=[O:21])[NH:17][C:16]1=[O:22].C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:4]2[C:3]=1[C:8](=[O:9])[N:14]([C:15]1([CH3:23])[CH2:20][CH2:19][C:18](=[O:21])[NH:17][C:16]1=[O:22])[C:5]2=[O:7]

Participants

5

Reactant 3

HCID 985004-Methyl-1,3-isobenzofurandioneHCID 517045Sodium AcetateHCID 219282523-Amino-3-methylpiperidine-2,6-dione hydrochloride

Product 1

HCID 99258974-Methyl-2-(2,6-dioxo-3-methyl-(3-piperidyl))isoindoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Methyl-2-(2,6-dioxo-3-methyl-(3-piperidyl))isoindoline-1,3-dione was prepared by the procedure of Example 1 from 3-methylphthalic anhydride (0.27 g, 1.7 mmol), 3-amino-3-methylpiperidine-2,6-dione hydrogen chloride (0.30 g, 1.7 mmol) and sodium acetate (0.15 g, 1.8 mmol) in acetic acid (10 mL). The product was a white solid (0.13 g, 27 % yield); mp, 248.0-250.0° C.; 1H NMR (DMSO-d6) δ1.89 (s, 3H, CH3), 2.01-2.08 (m, 1H, CHH), 2.49-2.70 (m, 3H, CHH, CH2), 2.55 (s, 3H, CH3), 7.62-7.74 (m, 3H, Ar), 10.99 (br s, 1H, NH); 13C NMR (DMSO-d6) δ17.0, 21.0, 28.6, 29.1, 58.6, 120.7, 127.5, 131.5, 134.2, 136.8, 137.2, 167.7, 168.6, 172.1, 172.3; Anal. Calcd. for C15H14N2O4+0.3 H2O: C, 61.77; H, 5.05; N, 9.60. Found: C, 62.05; H, 4.94; N, 9.20.

Sources & evidence

ORD record
ord-9527dce5fbc842c6920c0685bfb72ed2
Source dataset
uspto-grants-2002_06
Patent number
US06403613B1

Reaction notes

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