Isatin → 2,3-Dimethoxyindolo[2,1-b]quinazoline-6,12-dione

HRID 1756564Notes

Reaction equation

HRID 1756564 reaction equation
[CH3:1][O:2][C:3]1[C:14]([O:15][CH3:16])=[C:7]2C(O[C:11](=O)[NH:12][C:6]2=[CH:5][CH:4]=1)=O.Cl[C:18]1[CH:29]=[C:22]2[C:23]([O:25][C:26](=O)[NH:27][C:21]2=[CH:20][CH:19]=1)=[O:24].N1C2C(=CC=CC=2)C(=O)C1=O.FC1C=C2C(=CC=1)NC(=O)C2=O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][C:14]=1[O:15][CH3:16])[N:12]=[C:11]1[C:23](=[O:24])[C:22]3[C:21]([N:27]1[C:26]2=[O:25])=[CH:20][CH:19]=[CH:18][CH:29]=3

Participants

6

Reactant 4

HCID 7054IsatinHCID 784805-Chloroisatoic anhydrideHCID 2365665-FluoroisatinHCID 127623805,6-Dimethoxyisatoic anhydride

Product 1

HCID 4785712,3-Dimethoxyindolo[2,1-b]quinazoline-6,12-dioneYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using the procedure in Example 12, and substituting N-methylpyrrolidone (NMP) for N,N-dimethylformamide (DMF), 5,6-dimethoxyisatoic anhydride for 5-chloroisatoic anhydride and isatin for 5-fluoroisatin gave 367 mg (16%) of the title compound: mp 350° C. (dec); 1H NMR(CDCl3)δ 4.02-4.08 (d, 6H), 7.40-7.45 (m, 2H), 7.74-7.80 (m, 2H), 7.88-7.92 (m, 1H), 8.60-8.65 (d, 1H); MS (M+H)+ 308.

Sources & evidence

ORD record
ord-a8f428526e8340b5913d9845d9888c16
Source dataset
uspto-grants-1995_08
Patent number
US05441955

Reaction notes

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