Benzonitrile → 2-Phenyl[1,2,4]triazolo[1,5-a]pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-amino-pyridine (2.00 g, 21.0 mmol), copper (I) bromide (160 mg, 1.09 mmol), 1,10-phenanthroline monohydrate (225 mg, 1.12 mmol) and benzonitrile (25 mL) was heated in a 50-mL 3-necked flask to 130° C. During 27 h a gentle flow of (O2/N2 5:95) was bubbled through the reaction mixture (>99% conversion, HPLC method see below). The dark brown suspension was then cooled to 0-5° C. and filtered. The filtrate was evaporated at 60° C./0.1 mbar to dryness and the dark brown residue dissolved in DCM (30 mL). The organic solution was washed with water (30 mL), dried over sodium sulphate, filtered and evaporated to yield 6.07 g of crude 2-phenyl-[1,2,4]triazolo[1,5-a]pyridine containing approx. 4 g of residual benzonitrile.

Provenance & Evidence