HCID 3207460, compound → HCID 135797556, compound

Reaction equation

[NH2:1][C:2]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([CH:13]=2)=[CH:11][C:10]([O:15][CH3:16])=[C:9]([O:17][CH3:18])[CH:8]=3)[S:4][C:3]=1[C:19]([NH2:21])=[O:20].[N:22]([O-])=O.[Na+]>C(O)(=O)C.O>[CH3:18][O:17][C:9]1[C:10]([O:15][CH3:16])=[CH:11][C:12]2[CH:13]=[C:14]3[C:2]4[N:1]=[N:22][NH:21][C:19](=[O:20])[C:3]=4[S:4][C:5]3=[N:6][C:7]=2[CH:8]=1

Participants

Procedure

To a solution of 5.0 g of 3-amino-6,7-dimethoxythieno[2,3-b]quinoline-2-carboxamide in 1.5 liters of glacial acetic acid was added dropwise a solution of 4.0 g of sodium nitrite in 20 ml of water. The resulting mixture was stirred at room temperature for 16 hours. The solvent was then evaporated from the reaction mixture under reduced pressure to concentrate it to a volume of 300 ml. The solid which formed was separated by filtration to give 8,9-dimethoxy-1,2,3-triazino[4',5':4,5]thieno[2,3-b]quinolin-4(3H)-one. A small portion of this product was washed with hot tetrahydrofuran to give an off-white solid melting at greater than 230° C. with decomposition. The product obtained has the following structural formula ##STR3##