Beta-Alanine → 15728-05-9

HRID 858348Notes

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

Participants

Reactant 2

HCID 239Beta-Alanine

HCID 216313-Nitrophthalic anhydride

Product 1

HCID 84041115728-05-9Yield 80.1%

Procedure

3-nitrophthalic anhydride (0.5 g, 0.0026 mol) and β-alanine (0.23 g, 0.0026 mol) were refluxed as above overnight. The clear solution was purified as per 120 to yield 0.55 g (80%) 121 as a pale yellow powder: mp=146–148° C.; Rf 0.73 (A): Rf 0.87 (C): Rf 0.57 (D): 1H NMR (DMSO-d6) δ 2.60 (t, J=7.4 Hz, 2H), 3.78 (t, J=7.4 Hz, 2H), 8.07 (dd, J=7.5, 8.0 Hz, 1H), 8.16 (d, J=7.5 Hz, 1H), 8.27 (d, J=8.0, 1H); IR (cm−1): 2800–3200 (OH), 3097 (C═CH), 2620 (C—H), 1781 (C═O), 1725 (bs, C═O), 1617 (C═C), 1545 (N═O), 1468 (C═C), 1450 (C═C), 1395 (C—O), 1360 (N═O), 1235 (C—O), 723 (C═CH); MS m/z (rel intensity) 264 (76), 263 (100), 191 (90).

Workup

customThe clear solution was purified as per 120

Sources & evidence

ORD record: ord-32ad26638b6b49639ba1b7fbf18bf1e6
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148352B2

Reaction notes

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