Gamma-Aminobutyric Acid → 2-(3-Carboxypropyl)-1,3-dioxoisoindoline-5-carboxylic acid

HRID 992215Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[O:10][C:8](=O)[C:7]2=[CH:13][CH:14]=1)([OH:3])=[O:2].[NH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20]>>[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:15]([CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[C:8](=[O:10])[C:7]2=[CH:13][CH:14]=1)([OH:3])=[O:2]

Participants

Reactant 2

HCID 119Gamma-Aminobutyric Acid

HCID 11089Trimellitic anhydride

Product 1

HCID 8297292-(3-Carboxypropyl)-1,3-dioxoisoindoline-5-carboxylic acidYield 76.3%

Procedure

4-carboxyphthalic anhydride (1.0 g, 0.0052 mol) and 4-aminobutyric acid (0.54 g, 0.0052 mol) were refluxed as above for 7 hours. Crystallisation of the product from EtOH yielded 1.1 g (76%) of 102 as a white solid: mp=218-220° C.; Rf0.78 (A): Rf0.84 (C): Rf0.28 (D): 1H NMR (DMSO-d6); IR (cm−1): 2800-3250 (OH), 3050 (C═CH), 2680 (C—H), 1760 (C═O), 1712 (bs, C═O), 1560 (C═C), 1430 (C═C), 1397 (C—O), 1305 (C—O), 727 (C═CH); MS m/z (rel intensity) 277 (18), 276 (100).

Workup

customCrystallisation of the product from EtOH

Sources & evidence

ORD record: ord-305444cf15a746e0b467da7dc978cb2b
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06468990B1

Reaction notes

Loading…