Sodium Carbonate → 1-(4-Nitro-1,3-dioxoisoindolin-2-yl)propane-1,3-dicarboxylic acid

HRID 844216

Reaction equation

HRID 844216 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].C(=O)([O-])[O-].[Na+].[Na+].[N+:17]([C:20]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:21]=1[C:22](=[O:35])N(C(OCC)=O)[C:24]2=[O:29])([O-:19])=[O:18]>O>[N+:17]([C:20]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:21]=1[C:22](=[O:35])[N:1]([CH:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6])[C:24]2=[O:29])([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 33032L-Glutamic AcidHCID 108015374-Nitro-N-carboethoxyphthalimide

Product 1

HCID 3527981-(4-Nitro-1,3-dioxoisoindolin-2-yl)propane-1,3-dicarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of glutamic acid (10 mmol) and sodium carbonate (10.5 mmol) in water (50 mL) is added ethyl 4-nitro-1,3-dioxoisoindoline-2-carboxylate (10 mmol). The resulting mixture is stirred for 3 hours. The mixture is filtered. The filtrate is then acidified to pH 1 with 4 N hydrochloric acid to afford the 1-(4-nitro-1,3-dioxoisoindolin-2-yl)propane-1,3-dicarboxylic acid.

Workup

  1. filtrationThe mixture is filtered

Sources & evidence

ORD record
ord-95313c391a4048388051dd3f612d206b
Source dataset
uspto-grants-2002_04
Patent number
US06380239B1

Linked notes

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