4-Aminobenzoic Acid → HCID 746816, compound

HRID 858360Notes

Reaction equation

HRID 858360 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][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:5]=[C:6]2[C:11](=[O:12])[N:15]([C:16]3[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=3)[C:8](=[O:10])[C:7]2=[CH:13][CH:14]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 9784-Aminobenzoic AcidHCID 2309764-Nitrophthalic acid anhydride

Product 1

HCID 746816HCID 746816, compoundYield 81.3%

Procedure

4-nitrophthalic anhydride (0.25 g, 0.0013 mol) and p-aminobenzoic acid (0.18 g, 0.0013 mol) were refluxed as above overnight. The clear solution was purified as per 120 to yield 0.33 g(81%) 145 as a very pale dull yellow powder: mp=331–332° C.; Rf 0.86 (A): Rf 0.92 (C): Rf 0.56 (D): IR(cm−1): 2750–3150 (OH), 3116 (C═CH), 2684 (C—H), 1780 (C═O), 1730 (bs, C═O), 1622 (C═C), 1608 (C═C), 1543 (N═O), 1510 (C═C), 1434 (C═C), 1383 (C—O), 1350 (N═O), 1103 (C—O), 727 (C═CH); MS m/z (rel intensity) 311 (100), 267 (87).

Workup

  1. customThe clear solution was purified as per 120

Sources & evidence

ORD record
ord-472534bd3e0e418ab14bf16dc871b9a0
Source dataset
uspto-grants-2006_12
Patent number
US07148352B2

Reaction notes

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