5-Aminovaleric acid → HCID 18411561, compound

HRID 858342Notes

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

Participants

Reactant 2

HCID 1385-Aminovaleric acid

HCID 11089Trimellitic anhydride

Product 1

HCID 18411561HCID 18411561, compoundYield 99.7%

Procedure

4-carboxyphthalic anhydride (1.0 g, 0.0052 mol) and 5-aminopentanoic acid (0.61 g, 0.0052 mol) were refluxed as above overnight. Crystallisation of the product from EtOH yielded 1.51 g (72%) of 103 as a white solid: mp=223° C.; Rf 0.79 (A): Rf 0.92 (C): Rf 0.36 (D): IR (cm−1): 2750–3375 (OH), 3084 (C═CH), 2665 (C—H), 1767 (C═O), 1705 (bs, C═O), 1620 (C═C), 1486 (C═C), 1402 (CH2), 1382 (C—O), 1302 (C—O), 732 (C═CH); MS m/z (rel intensity) 291 (15), 290 (100).

Workup

customCrystallisation of the product from EtOH

Sources & evidence

ORD record: ord-a36b12f62b9a42a9a8a6094aefb23013
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148352B2

Reaction notes

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