Benzene → 5(2-Cyanophenyl)indazole

Participants

Reaction Conditions

Reaction Steps

2-(4-Acetamino-3-methylphenyl)benzonitrile (15.2 mmole, 3.8 g) was dissolved in 50 ml acetic acid and treated for 1 hour at room temperature with a scream of gaseous N2O5 generated by the addition of nitric acid to sodium nitrite. Benzene and brine were added to the reaction. The organic layer was separated, dried and warmed gently on a rotorvap (45° C.) for 1 hour. The solution was concentrated. Ether and saturated sodium bicarbonate were added. The organic phase was dried and concentrated. The residue was chromatographed over silica gel eluded with 50% ether in hexane to yield 240 mg of 5(2-cyanophenyl)indazole. (MS)

Provenance & Evidence