Glycine → 2-(5-nitro-1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)acetic acid

HRID 858355Notes

Reaction equation

[N+: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)([O-:3])=[O:2].[NH2:15][CH2:16][C:17]([OH:19])=[O:18]>>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:15]([CH2:16][C:17]([OH:19])=[O:18])[C:8](=[O:10])[C:7]2=[CH:13][CH:14]=1)([O-:3])=[O:2]

Participants

Reactant 2

HCID 750Glycine

HCID 2309764-Nitrophthalic acid anhydride

Product 1

HCID 2727372-(5-nitro-1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)acetic acidYield 86.1%

Procedure

4-nitrophthalic anhydride (0.25 g, 0.0013 mol) and glycine (0.097 g, 0.0013 mol) were refluxed as above overnight. The clear solution was purified as per 120 to yield 0.28 g (86%) 140 as very pale yellow crystals: mp=195–96° C.; Rf 0.79 (A): Rf 0.75 (B): Rf 0.28 (D): IR(cm−1): 2811–3150 (OH), 3115 (C═CH), 1787 (C═O), 1730 (bs, C═O), 1622 (C═C), 1551 (N═O), 1412 (C═C), 1391 (C—O), 1351 (N═O), 1117 (C—O), 720 (C—CH); MS m/z (rel intensity) 250 (7), 249 (62), 205 (100), 122 (10).

Workup

customThe clear solution was purified as per 120

Sources & evidence

ORD record: ord-80b66e58e4b64a98ad43df9023cc60a7
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148352B2

Reaction notes

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