Tetrahydrofuran → HCID 14171581, compound

Participants

Reaction Steps

Diazomethane was prepared by adding Diazald® (21.4 g) in 200 ml of ether to potassium hydroxide (5.0 g) in 20 ml of 50% ethanol/water solution and then distilling. This procedure was followed three times to give a solution of diazomethane (16.25 g) in ether which was then added to a stirred slurry of 7-chloropyrrolo[1,2-b]cinnolin-10(5H)-one (37.0 g) in 250 ml of tetrahydrofuran. The mixture was allowed to stand at room temperature for 48 hours and then the volatiles were removed. The residue was taken up in dichloromethane and washed several times with water. The organic layer was dried (MgSO4), filtered and concentrated to a dark orange powder. The powder was purified by flash chromatography (silica, dichloromethane) to give 18.35 g of an orange powder. A five gram portion of this powder was recrystallized from ether to give 4.3 g of an orange fibrous material, mp 128°-129°.

Provenance & Evidence