Beta-Alanine → HCID 2304977, compound

HRID 992214Notes

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

Participants

Reactant 2

HCID 239Beta-Alanine

HCID 11089Trimellitic anhydride

Product 1

HCID 2304977HCID 2304977, compoundYield 100.1%

Procedure

4-carboxyphthalic anhydride (1.0 g, 0.0052 mol) and β-alanine (0.46, 0.0052 mol) were refluxed as above for 7 hours. Crystallisation of the product from EtOH yielded 1.37 g (78%) of 101 as a white solid: mp=240-242° C.; Rf0.77 (A): Rf0.67 (B): Rf0.33 (D): 1H NMR (DMSO-d6); MS m/z (rel intensity) 263 (14), 262 (100); IR (cm−1): 2800-3250 (OH), 1350 (C═CH), 2671 (C—H), 1777 (C═O), 1725 (C═O), 1705 (C═O), 1620 (C═C), 1452 (C═C), 1385(C—O), 1226 (C—O), 731 (C═CH). MS m/z (rel intensity) 263 (14), 262 (100).

Workup

customCrystallisation of the product from EtOH

Sources & evidence

ORD record: ord-957e15f4548942f181b90c5e26fafd97
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06468990B1

Reaction notes

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