3-Nitrophthalic anhydride → 1-(4-Nitro-1,3-dioxoisoindolin-2-yl)propane-1,3-dicarboxylic acid

HRID 844228Notes

Reaction equation

[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([O:9][C:10](=[O:11])[C:5]=12)=O)([O-:3])=[O:2].[NH2:15][C@H:16]([C:22]([OH:24])=[O:23])[CH2:17][CH2:18][C:19]([OH:21])=[O:20]>CN(C=O)C>[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:5]=1[C:10](=[O:11])[N:15]([CH:16]([C:22]([OH:24])=[O:23])[CH2:17][CH2:18][C:19]([OH:21])=[O:20])[C:7]2=[O:9])([O-:3])=[O:2]

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 3-nitrophthalic anhydride (1.5 g, 7.77 mmol) and L-glutamic acid (1.2 g, 7.77 mmol) in DMF (15 mL) is heated at 85° C. for 6 hours. The mixture is concentrated in vacuo and the residue is purified by chromatography (silica gel, CH2Cl2:CH3OH 95:5) to give 1-(4-nitro-1,3-dioxoisoindolin-2-yl)propane-1,3-dicarboxylic acid (1.51 g, 60%); 1H NMR (DMSO-d6) δ8.32 (d, J=7.9 Hz, 1H), 8.21 (d, J=7.3 Hz, 1H), 8.10 (t, J=7.8 Hz, 1H), 4.88-4.82 (dd, J=3.0 and 10.0 Hz, 1H), 2.35-2.20 (m, 4H).

Workup

concentrationThe mixture is concentrated in vacuo
customthe residue is purified by chromatography (silica gel, CH2Cl2:CH3OH 95:5)

Sources & evidence

ORD record: ord-e155c4caaa6c464c99b6b3004c3c2474
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06380239B1

Reaction notes

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