3-Aminobenzoic Acid → HCID 695081, compound

HRID 858345Notes

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][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19]([OH:21])=[O:20]>>[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:15]([C:16]3[CH:24]=[CH:23][CH:22]=[C:18]([C:19]([OH:21])=[O:20])[CH:17]=3)[C:8](=[O:10])[C:7]2=[CH:13][CH:14]=1)([OH:3])=[O:2]

Participants

Reactant 2

HCID 74193-Aminobenzoic Acid

HCID 11089Trimellitic anhydride

Product 1

HCID 695081HCID 695081, compoundYield 74.8%

Procedure

4-carboxyphthalic anhydride (1.0 g, 0.0052 mol) and m-aminobenzoic acid (0.714 g, 0.0052 mol) were refluxed as above overnight. Crystallisation of the product from MeOH yielded 1.21 g (72%) of 106 as a white solid: mp=>380° C.; Rf 0.87 (A): Rf 0.75 (C): Rf 0.27 (D):IR (cm−1): 2700–3125 (OH), 3090 (C═CH), 2665 (C—H), 1780 (C═O), 1731 (C═O), 1699 (C═O), 1610 (C═C), 1589 (C═C), 1484 (C═C), 1452 (C═C), 1383 (C—O), 1310 (C—O), 1222 (C—O), 722 (C═CH); MS m/z (rel intensity) 311 (22), 310 (100).

Workup

customCrystallisation of the product from MeOH

Sources & evidence

ORD record: ord-24a9cb2ae79a48179cdb1cfd6c83a5e4
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148352B2

Reaction notes

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