5-Chloroisatoic anhydride → HCID 478578, compound

HRID 1756571Notes

Reaction equation

HRID 1756571 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].[I:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19](=O)[C:18]2=[O:25].FC1C=C2C(=CC=1)NC(=O)C2=O>>[I:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]1[C:19](=[N:11][C:5]3[C:6]([C:7]1=[O:8])=[CH:13][CH:2]=[CH:3][CH:4]=3)[C:18]2=[O:25]

Participants

4

Reactant 3

HCID 784805-Chloroisatoic anhydrideHCID 886955-IodoisatinHCID 2365665-Fluoroisatin

Product 1

HCID 478578HCID 478578, compoundYield 31%

Procedure

Using the procedure in Example 12 and substituting isatoic anhydride for 5-chloroisatoic anhydride and 5-iodoisatin for 5-fluoroisatin gave the title compound in 31% yield: mp 296.5°-297.3° C.; 1H NMR (300MHz, DMSO-d6) δ 8.16-8.36 (m, 4H) 7.96 (2, H) 7.70-7.83 (m, 1H); MS (M+H)+ 374.

Sources & evidence

ORD record
ord-cbd52ed0f5f84e6ba918d1bb79d4d0a0
Source dataset
uspto-grants-1995_08
Patent number
US05441955

Reaction notes

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