HCID 869878, compound → HCID 11821097, compound

Participants

Reaction Steps

To 200 ml of conc. hydrochloric acid was added 21.1 g of stannous chloride under ice cooling, and 9.0 g of 5-nitro-2-(3-pyridylmethyl)-1H-isoindole-1,3 (2H)-dione was added. The reaction mixture was stirred at room temperature for 15 minutes and stirred at 80° C. for 30 minutes. After cooling, the mixture was filtered, and the resultant solid was mixed with water and made alkaline with aqueous ammonia. To this mixture was added 500 ml of tetrahydrofuran, and the resultant mixture was filtered with celite. The filtrate was shaken with methylene chloride. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resultant residue was chromatographed on a column of silica gel, eluting with ethyl acetate and hexane (2:1) to give 7.4 g of the titled compound.

Provenance & Evidence