Trimellitic anhydride → 2-[4-Methoxy-5-(5-phenylbenzoxazol-2-yl)phenyl]-1,3-dioxo-2,3-dihydro-1h-isoindole-5-carboxylic acid

HRID 722522Notes

Reaction equation

HRID 722522 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:15][C:13]=3[N:14]=2)[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[CH:25]1[C:30]([C:31]([OH:33])=[O:32])=[CH:29][C:28]2[C:34]([O:36][C:37](=O)[C:27]=2[CH:26]=1)=[O:35]>>[CH3:9][O:8][C:5]1[C:4]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[CH:15][C:13]=3[N:14]=2)=[CH:3][C:2]([N:1]2[C:34](=[O:35])[C:28]3[C:27](=[CH:26][CH:25]=[C:30]([C:31]([OH:33])=[O:32])[CH:29]=3)[C:37]2=[O:36])=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 11089Trimellitic anhydrideHCID 218844572-(3-Amino-6-methoxyphenyl)-5-phenylbenzoxazole

Product 1

HCID 218846292-[4-Methoxy-5-(5-phenylbenzoxazol-2-yl)phenyl]-1,3-dioxo-2,3-dihydro-1h-isoindole-5-carboxylic acid

Procedure

Prepared by the method of Example 15f), from 2-(3-amino-6-methoxyphenyl)-5-phenylbenzoxazole (420 mg, 1.42 mmol) and 1,2,4-benzenetricarboxylic anhydride (273 mg, 1.42 mmol) the title compound was obtained, (460 mg, 66%). 1H NMR (DMSO) δ 13.85(s, 1H), 8.51(dd, 1H), 8.41(s, 1H), 8.29(d, 1H), 8.16(m, 2H), 7.95(d, 1H), 7.81(m, 4H), 7.58(m, 2H), 7.54(d, 1H), 7.48(d, 1H), 4.12(s, 3H). MS 491 m/z (M+H)+.

Sources & evidence

ORD record
ord-1d95b5ed846e44bb81ee2893b6537179
Source dataset
uspto-grants-2006_11
Patent number
US07138425B2

Reaction notes

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