5-Methoxyisatin → HCID 478576, compound

HRID 1756569Notes

Reaction equation

Cl[C:2]1[CH:13]=[C:6]2[C:7](OC(=O)[NH:11][C:5]2=[CH:4][CH:3]=1)=[O:8].[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20](=O)[C:19]2=[O:26].FC1C=C2C(=CC=1)NC(=O)C2=O>>[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]1[C:20](=[N:11][C:5]3[C:6]([C:7]1=[O:8])=[CH:13][CH:2]=[CH:3][CH:4]=3)[C:19]2=[O:26]

Participants

Reactant 3

HCID 383335-Methoxyisatin

HCID 784805-Chloroisatoic anhydride

HCID 2365665-Fluoroisatin

Product 1

HCID 478576HCID 478576, compoundYield 24%

Procedure

Using the procedure in Example 12 and substituting isatoic anhydride for 5-chloroisatoic anhydride and 5-methoxyisatin for 5-fluoroisatin gave the title compound in 24% yield: mp 267.6°-269° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.28 (d, 1H) 8.25 (d, 1H) 7.93 (d, 2H) 7.68-7.78 (m, 1H) 7.37-7.46 (m, 2H) 3.88 (s, 3H); MS (M+H)+ 279.

Sources & evidence

ORD record: ord-534732cd727e4dd99e6ffd01f335a4b2
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05441955

Reaction notes

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