Trimellitic anhydride → 2-(5-(5-(Benzo[d][1,3]dioxol-5-yl)benzo[d]oxazol-2-yl)-2-methoxyphenyl)-1,3-dioxoisoindoline-5-carboxylic acid

HRID 722496Notes

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][C:22]5[O:25][CH2:26][O:27][C:21]=5[CH:20]=4)=[CH:15][C:13]=3[N:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH:28]1[C:33]([C:34]([OH:36])=[O:35])=[CH:32][C:31]2[C:37]([O:39][C:40](=O)[C:30]=2[CH:29]=1)=[O:38]>>[CH3:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][C:22]5[O:25][CH2:26][O:27][C:21]=5[CH:20]=4)=[CH:15][C:13]=3[N:14]=2)=[CH:3][C:2]=1[N:1]1[C:37](=[O:38])[C:31]2[C:30](=[CH:29][CH:28]=[C:33]([C:34]([OH:36])=[O:35])[CH:32]=2)[C:40]1=[O:39]

Participants

Reactant 2

HCID 11089Trimellitic anhydride

HCID 69585101HCID 69585101, compound

Product 1

HCID 443396982-(5-(5-(Benzo[d][1,3]dioxol-5-yl)benzo[d]oxazol-2-yl)-2-methoxyphenyl)-1,3-dioxoisoindoline-5-carboxylic acid

Procedure

Prepared by the method of Example 15f), from 2-(3-amino-4-methoxyphenyl-5-[3,4-(methylenedioxy)phenyl]benzoxazole (120 mg, 0.33 mmol) and 1,2,4-benzenetricarboxylic anhydride (70 mg, 0.36 mmol) the title compound was obtained (82 mg, 46%). 1H NMR (DMSO) δ 8.45(dd, 1H), 8.37–8.32(m, 3H), 8.12(d, 1H), 7.96(d, 1H), 7.79(d, 1H), 7.63(dd, 1H), 7.49(d, 1H), 7.33(d, 1H), 7.20(dd, 1H), 7.02(d, 1H), 6.06(2H, s), 3.88(s, 3H). MS m/z 535.0 (M+H)+.

Sources & evidence

ORD record: ord-1c3ed8cdb83b4f2686444b4d52ce9314
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138425B2

Reaction notes

Loading…