3-Aminobenzoic Acid → HCID 554931, compound

HRID 858361Notes

Reaction equation

HRID 858361 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:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19]([OH:21])=[O:20]>>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:15]([C:16]3[CH:24]=[CH:23][CH:22]=[C:18]([C:19]([OH:21])=[O:20])[CH:17]=3)[C:8](=[O:10])[C:7]2=[CH:13][CH:14]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 74193-Aminobenzoic AcidHCID 2309764-Nitrophthalic acid anhydride

Product 1

HCID 554931HCID 554931, compoundYield 74%

Procedure

4-nitrophthalic anhydride (0.25 g, 0.0013 mol) and m-aminobenzoic acid (0.18 g, 0.0013 mol) were refluxed as above overnight. The clear solution was purified as per 120 to yield 0.30 g (74%) 146 as a very pale dull yellow powder: mp=368–370° C.; Rf 0.83 (A): Rf 0.93 (C): Rf 0.53 (D): IR (cm−1): 2700–3280 (OH), 3122 (C═CH), 2687 (C—H), 1781 (C═O), 1727 (bs, C═O), 1622 (C═C), 1588 (C═C), 1546 (N═O), 1461 (C═C), 1420 (C═C), 1386 (C—O), 1350 (N═O), 1113 (C—O), 727 (C═CH); MS m/z (rel intensity) 311 (68), 285 (46), 267 (46), 191 (100).

Workup

  1. customThe clear solution was purified as per 120

Sources & evidence

ORD record
ord-47aab5a53d93470588721269f23fc79d
Source dataset
uspto-grants-2006_12
Patent number
US07148352B2

Reaction notes

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