Hydrochloric Acid → (2-Amino-5,6,7,8-tetrahydroquinolin-3-yl)(p-tolyl)methanone

Participants

Reaction Steps

To a solution of 2-amino-5,6,7,8-tetrahydroquinoline-3-carbonitrile (1.2 g; 6.93 mmol) in dry tetrahydrofurane (70 mL) under nitrogen atmosphere was slowly added a solution of p-tolylmagnesium bromide (1M in THF) (35 mL; 35 mmol). The resulting solution was stirred at room temperature for 3 h and heated at 50° C. for 3 h. A solution of hydrochloric acid 3N (140 mL) was added to hydrolyse the intermediate imine and the reaction mixture was heated to reflux for 3 h. After cooling at 0° C., the reaction mixture was basified with a solution of sodium hydroxide 6N. The product was extracted with dichloromethane (200 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 (10-100%) in dichloromethane as eluent furnished 1.51 g (82%) of (2-amino-5,6,7,8-tetrahydroquinolin-3-yl)(p-tolyl)methanone as a bright yellow solid. ESI/APCI(+): 267 (M+H).

Provenance & Evidence