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

HRID 618699Notes

Reaction equation

HRID 618699 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-1aef9a3d7e7940b19b149030b32e9f93
Source dataset
uspto-grants-1999_09
Patent number
US05955476

Reaction notes

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