Phthalic Anhydride → Dimethyl 2-(1,3-dioxo-1,3-dihydro-2h-isoindol-2-yl)pentanedioate

HRID 363438Notes

Reaction equation

HRID 363438 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C@H:4]([CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])[NH2:5].[C:13]1(=O)[O:18][C:16](=[O:17])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12>C(O)(=O)C>[O:17]=[C:16]1[C:15]2[C:14](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13](=[O:18])[N:5]1[CH:4]([CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])[C:3]([O:2][CH3:1])=[O:12]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 93032Dimethyl glutamate

Product 1

HCID 272791Dimethyl 2-(1,3-dioxo-1,3-dihydro-2h-isoindol-2-yl)pentanedioate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred mixture of L-glutamic acid dimethyl ester (2.0 g, 11.4 mmol) and phthalic anhydride (1.7 g, 11.4 mmol) in acetic acid (30 mL) is heated to refluxed for one hour. The solvent is removed in vacuo to yield dimethyl 2-(1,3-dioxoisoindolin-2-yl)-pentane-1,5-dioate which is further purified through chromatography.

Workup

  1. temperatureis heated
  2. temperatureto refluxed for one hour
  3. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-0ad96a8339c542f2a9edc126866535f9
Source dataset
uspto-grants-1999_02
Patent number
US05874448

Reaction notes

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