Gamma-Aminobutyric Acid → 4-(4-nitro-1,3-dioxoisoindolin-2-yl)butanoic acid

HRID 858349Notes

Reaction equation

HRID 858349 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][C:19]([OH:21])=[O:20]>>[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([N:15]([CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[C:10](=[O:11])[C:5]=12)=[O:9])([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 119Gamma-Aminobutyric AcidHCID 216313-Nitrophthalic anhydride

Product 1

HCID 7654724-(4-nitro-1,3-dioxoisoindolin-2-yl)butanoic acidYield 79%

Procedure

3-nitrophthalic anhydride (0.5 g, 0.0026 mol) and 4-aminobutyric acid (0.268 g, 0.0026 mol) were refluxed as above overnight. The clear solution was purified as per 120 to yield 0.57 g (79%) 122 as a very pale orange powder: mp=144–146° C.; Rf 0.62 (A): Rf 0.87 (C): Rf 0.78(D): IR (cm−1): 3000–3250 (OH), 3219 (C═CH), 2953 (C—H), 1778 (C═O), 1716 (C═O), 1667 (C═O), 1615 (C═C), 1548 (N═O), 1442 (C═C), 1395 (C—O), 1355 (N═O), 1189 (C—O), 723 (C═CH); MS m/z (rel intensity) 313 (100), 278 (65), 277 (42), 191 (71).

Workup

  1. customThe clear solution was purified as per 120

Sources & evidence

ORD record
ord-824be076eb084710846b8edff945b2e8
Source dataset
uspto-grants-2006_12
Patent number
US07148352B2

Reaction notes

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