5-Chloroisatoic anhydride → 7-Chloroindolo[2,1-b]quinazoline-6,12-dione

HRID 1756577Notes

Reaction equation

HRID 1756577 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].[Cl:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[C:17](=[O:25])[C:18](=O)[NH:19]2.FC1C=C2C(=CC=1)NC(=O)C2=O>>[Cl:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[C:17](=[O:25])[C:18]1[N:19]2[C:7](=[O:8])[C:6]2[C:5](=[CH:4][CH:3]=[CH:2][CH:13]=2)[N:11]=1

Participants

4

Reactant 3

HCID 784805-Chloroisatoic anhydrideHCID 960474-ChloroisatinHCID 2365665-Fluoroisatin

Product 1

HCID 4786477-Chloroindolo[2,1-b]quinazoline-6,12-dioneYield 16%

Procedure

Using the procedure in Example 12 and substituting isatoic anhydride for 5-chloroisatoic anhydride and 4-chloroisatin for 5-fluoroisatin gave the title compound in 16% yield: mp 294°-295.7° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.49 (d, 1H) 8.33 (d, 1H) 7.97 (d, 2H) 7.81-7.90 (m, 1H) 7.72-7.80 (m, 1H) 7.52 (d, 1H); MS (M+H)+ 283.

Sources & evidence

ORD record
ord-8090b1339eae431dac13d7d02e14ca12
Source dataset
uspto-grants-1995_08
Patent number
US05441955

Reaction notes

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