HCID 3207460, compound → HCID 135797556, compound

HRID 2413325Notes

Reaction equation

HRID 2413325 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

5

Reactant 2

HCID 3207460HCID 3207460, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 135797556HCID 135797556, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

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##

Workup

  1. customThe solvent was then evaporated from the reaction mixture under reduced pressure
  2. concentrationto concentrate it to a volume of 300 ml
  3. customThe solid which formed
  4. customwas separated by filtration

Sources & evidence

ORD record
ord-2ebe86ba28a94e94b39aad7b7b0a26fb
Source dataset
uspto-grants-1985_01
Patent number
US04496725

Reaction notes

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