6-Aminohexanoic Acid → 6-(4-Nitro-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)hexanoic acid

HRID 858351Notes

Reaction equation

HRID 858351 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][CH2:20][C:21]([OH:23])=[O:22]>>[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][CH2:20][C:21]([OH:23])=[O:22])[C:10](=[O:11])[C:5]=12)=[O:9])([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 5646-Aminohexanoic AcidHCID 216313-Nitrophthalic anhydride

Product 1

HCID 3035826-(4-Nitro-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)hexanoic acidYield 95%

Procedure

3-nitrophthalic anhydride (0.5 g, 0.0026 mol) and 6-aminohexanoic acid (0.34 g, 0.0026 mol) were refluxed as above overnight. The clear solution was purified as per 120 to yield 0.75 g (95%) 124 as a pale yellow powder: mp=144° C.; Rf 0.68 (A): Rf 0.89 (C): Rf 0.71 (D): IR (cm−1): 2800–3180 (OH), 3096 (C═CH), 2620 (C—H), 1777 (C═O), 1723 (bs, C═O), 1617 (C═C), 1543 (N═O), 1468 (C═C), 1442 (C═C), 1395 (C—O), 1359 (N═O), 1057 (C—O), 723 (C═CH); MS m/z (rel intensity) 305 (100), 191 (17).

Workup

  1. customThe clear solution was purified as per 120

Sources & evidence

ORD record
ord-e259c610334d4d65b2220163be4856e7
Source dataset
uspto-grants-2006_12
Patent number
US07148352B2

Reaction notes

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