Anthranilic Acid → HCID 4393655, compound

HRID 858354Notes

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][CH:22]=[CH:21][C:17]=1[C:18]([OH:20])=[O:19]>>[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][CH:22]=[CH:21][C:17]=3[C:18]([OH:20])=[O:19])[C:10](=[O:11])[C:5]=12)=[O:9])([O-:3])=[O:2]

Participants

Reactant 2

HCID 227Anthranilic Acid

HCID 216313-Nitrophthalic anhydride

Product 1

HCID 4393655HCID 4393655, compoundYield 21%

Procedure

3-nitrophthalic anhydride (1.0 g, 0.0052 mol) and o-aminobenzoic acid (0.71 g, 0.0052 mol) were refluxed as above for four days. The clear solution was purified as per 120 to yield 0.34 g (21%) 127 as pale orange grains: mp=190–192° C.; Rf 0.74 (A): Rf 0.87 (C): Rf 0.62 (E): IR (cm−1): 2700–3300 (OH), 3093 (C═CH), 2620 (C—H), 1718 (C═O), 1681 (bs, C═O), 1609 (C═C), 1592 (C═O), 1534 (N═O), 1482 (C═C), 1451 (C═C), 1360 (N═O), 1316 (C—O), 1257 (C—O), 771 (C═CH); MS m/z (rel intensity) 311 (50), 285 (100), 241 (55), 122 (45).

Workup

customThe clear solution was purified as per 120

Sources & evidence

ORD record: ord-2aa881564e0d4a9b9b6c0743fbe18669
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148352B2

Reaction notes

Loading…