5-Aminovaleric acid → HCID 2049944, compound

HRID 858350Notes

Reaction equation

[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([O:9][C:10](=[O:11])[C:5]=12)=O)([O-:3])=[O:2].[NH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21]>>[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([N:15]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C:10](=[O:11])[C:5]=12)=[O:9])([O-:3])=[O:2]

Participants

Reactant 2

HCID 1385-Aminovaleric acid

HCID 216313-Nitrophthalic anhydride

Product 1

HCID 2049944HCID 2049944, compoundYield 73%

Procedure

3-nitrophthalic anhydride (0.5 g, 0.0026 mol) and 5-aminopentanoic acid (0.30 g, 0.0026 mol) were refluxed as above overnight. The clear solution was purified as per 120 to yield 0.55 g (73%) 123 as pale yellow flat crystals: mp=158–160° C.; Rf 0.69 (A): Rf 0.90 (C): Rf 0.73 (D): 1H NMR (DMSO-d6) δ 1.53 (m, 2H), 1.58 (m, 2H), 2.24 (t, J=7.1 Hz, 2H), 3.57 (t, J=6.7 Hz, 2H), 8.04 (dd, J=8.0, 7.5 Hz, 1H), 8.16 (d, J=7.5 Hz, 1H), 8.27 (d, J=8.0 Hz, 1H); IR (cm−1): 2800–3130 (OH), 3096 (C═CH), 2691 (C—H), 1774 (C═O), 1723 (bs, C═O), 1616 (C═C), 1543 (N═O), 1466 (C═C), 1443 (C═C), 1396 (C—O), 1358 (N═O), 1209 (C—O), 1050 (C—O), 722 (C═CH); MS m/z (rel intensity) 291 (92), 247 (31), 191 (100).

Workup

customThe clear solution was purified as per 120

Sources & evidence

ORD record: ord-904bd94aa107430db8228d3ebded322b
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148352B2

Reaction notes

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