Trimellitic anhydride → HCID 777054, compound

HRID 992220Notes

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][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=1>>[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:15]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:24][CH:25]=3)[C:8](=[O:10])[C:7]2=[CH:13][CH:14]=1)([OH:3])=[O:2]

Participants

Reactant 2

HCID 11089Trimellitic anhydride

HCID 655264-(Aminomethyl)Benzoic Acid

Product 1

HCID 777054HCID 777054, compoundYield 79.2%

Procedure

4-carboxyphthalic anhydride (0.5 g, 0.0026 mol) and 4-(aminomethyl)benzoic acid (0.39 g, 0.0026 mol) were refluxed as above overnight. Crystallisation of the product from 1,4-dioxane/H2O yielded 0.67 g (79%) of 108 as a white solid: mp=365-366° C.; Rf0.76 (A): Rf0.71 (C): Rf0.50 (D): IR (cm−1): 2800-3100 (OH), 3071 (C═CH), 2678 (C—H), 1782 (C═O), 1712 (bs, C═O), 1611 (C═C), 1577 (C═C), 1428 (C═C), 1391 (C—O), 1300 (C—O), 1105 (C—O), 734 (C═CH); MS m/z (rel intensity) 325 (20), 324 (100).

Workup

customCrystallisation of the product from 1,4-dioxane/H2O

Sources & evidence

ORD record: ord-872864bd952a481f882b5d9ea9765468
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06468990B1

Reaction notes

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