Hydrochloric Acid → HCID 69673238, compound

Participants

Reaction Steps

To a solution of 2-aminoquinoline-3-carbonitrile (1.86 g; 11 mmol) in dry tetrahydrofurane (110 mL) under a nitrogen atmosphere was slowly added a solution of p-tolylmagnesium bromide (1M in THF) (55 mL; 55 mmol). The resulting solution was stirred at room temperature for 4 h. A solution of hydrochloric acid 3N (220 mL) was added to hydrolyse the intermediate imine and the reaction mixture was heated to reflux for 2 h and then stirred at room temperature for 18 h. After cooling to 0° C., the reaction mixture was basified with a solution of sodium hydroxide 6N. The product was extracted with ethyl acetate (160 mL) and the organics were dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (5-100%) in dichloromethane as eluent furnished 2.6 g (90%) of (2-aminoquinolin-3-yl)(p-tolyl)methanone as an ochre solid. ESI/APCI(+): 263 (M+H).

Provenance & Evidence