Anthranilic Acid → HCID 746608, compound

HRID 858362Notes

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][CH:22]=[CH:21][C:17]=1[C:18]([OH:20])=[O:19]>>[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]=[CH:21][C:17]=3[C:18]([OH:20])=[O:19])[C:8](=[O:10])[C:7]2=[CH:13][CH:14]=1)([O-:3])=[O:2]

Participants

Reactant 2

HCID 227Anthranilic Acid

HCID 2309764-Nitrophthalic acid anhydride

Product 1

HCID 746608HCID 746608, compoundYield 15%

Procedure

4-nitrophthalic anhydride (0.5 g, 0.0026 mol) and o-aminobenzoic acid (0.36 g, 0.0026 mol) were refluxed as above for four days. The clear solution was purified as per 120 with an additional final crystallisation from acetone/H2O to yield 0.12 g (15%) 147 as a very pale dull yellow powder: mp=242–243° C.; Rf 0.80 (A): Rf 0.88 (C): Rf 0.49 (D): IR (cm−1): 2725–3100 (OH), 3071 (C═CH), 2646 (C—H), 1786 (C═O), 1730 (C═O), 1693 (C═O), 1620 (C═C), 1601 (C═C), 1538 (N═O), 1491 (C═C), 1452 (C═C), 1383 (C—O), 1345 (N═O), 1123 (C—O), 723 (C═CH); MS m/z (rel intensity) 311 (33), 267 (76), 241 (54), 136 (100).

Workup

customThe clear solution was purified as per 120 with an additional final
customcrystallisation from acetone/H2O

Sources & evidence

ORD record: ord-8e1ad9a14fd049fdbab5cc1498fce377
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148352B2

Reaction notes

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