5-Chloroisatoic anhydride → HCID 478573, compound

HRID 1756567Notes

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].[N+:14]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21](=O)[C:20]2=[O:27])([O-:16])=[O:15].FC1C=C2C(=CC=1)NC(=O)C2=O>>[N+:14]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]1[C:21](=[N:11][C:5]3[C:6]([C:7]1=[O:8])=[CH:13][CH:2]=[CH:3][CH:4]=3)[C:20]2=[O:27])([O-:16])=[O:15]

Participants

Reactant 3

HCID 784805-Chloroisatoic anhydride

HCID 2365665-Fluoroisatin

HCID 46692505-Nitroisatin

Product 1

HCID 478573HCID 478573, compoundYield 18%

Procedure

Using the procedure in Example 12 and substituting isatoic anhydride for 5-chloroisatoic anhydride and 5-nitroisatin for 5-fluoroisatin gave the title compound in 18% yield: mp 302.2°-303° C.; 1H NMR (300 MHz, CDCl3) δ 8.88 (d, 1H) 8.77 (d, 1H) 8.66-8.74 (m, 1H) 8.46-8.52 (m, 1H) 8.09 (d, 1H) 7.88-7.98 (m, 1H) 7.72-7.80 (m, 1H); MS (M+H)+ 293.

Sources & evidence

ORD record: ord-52c9810c610d46659a2ff184bd66cad8
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05441955

Reaction notes

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