Tetrahydrofuran → HCID 12149035, compound

Participants

Reaction Steps

2 ml of thionyl chloride were added to a solution of 3-(2-nitrophenyl)thiophen-2-carboxylic acid (9) (3.5 g, 14 mmol) in 20 ml of anhydrous benzene and the mixture was refluxed for 2 hrs. The solvent and the excess thionyl chloride were removed under vacuum and the residue was taken up using 50 ml of THF, and NaN3 (1.37 g, 21 mmol) in 10 ml of water was added rapidly to this stirred solution at 0° C. The mixture was left for 1 hr at room temperature with stirring, poured into 100 ml of ice and water and extracted with ethyl ether (4×50 ml), the separated organic layer was dried over anhydrous sodium sulphate and leaving it for 2 hrs with stirring. It was evaporated under vacuum and coevaporated with anhydrous benzene (3×50 ml). It is evaporated and the residue was solubilized in 60 ml of o-dichlorobenzene and refluxed using a Dean-Stark apparatus. The mixture was left under reflux for 20 hrs with stirring, then cooled and evaporated. The mixture was subjected to flash chromatography, and elution with chloroform yielded the compound 9-nitrothieno-[2,3-c]-isoquinolin-5(4H)-one (0.075 g, 2.2% yield) as a yellow solid (M.Pt. 255-258° C.).

Provenance & Evidence