4-Aminobenzoic Acid → 4-(4-Nitro-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)benzoic acid
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][C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1>>[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([N:15]([C:16]3[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=3)[C:10](=[O:11])[C:5]=12)=[O:9])([O-:3])=[O:2]Participants
3
Procedure
3-nitrophthalic anhydride (0.79 g, 0.0041 mol) and p-aminobenzoic acid (0.56 g, 0.0041 mol) were refluxed as above overnight. Concentration of the solution under vacuum by rotary evaporator and crystallisation of the product from EtOH/H2O yielded 1.1 g (68%) of 125 as a vibrant light yellow powder: mp=338–340° C.; Rf 0.76 (A): Rf 0.89 (C): Rf 0.66 (D): R (cm−1): 2750–3125 (OH), 3091 (C═CH), 2671 (C—H), 1782 (C═O), 1736 (C═O), 1693 (C═O), 1610 (C═C), 1585 (C═C), 1529 (N═O), 1513 (C═C), 1433 (C═C), 1378 (C—O), 1360 (N═O), 1291 (C—O), 766 (C═CH); MS m/z (rel intensity) 311 (100), 267 (25), 191 (15).
Workup
- customConcentration of the solution under vacuum by rotary evaporator and crystallisation of the product from EtOH/H2O
Sources & evidence
- ORD record
- ord-abe64b1ed0834e8c837a4ff8dc6ce887
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07148352B2
Reaction notes
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