Acetyl chloride → HCID 18659970, compound

Participants

Reaction Steps

Diisopropylethylamine (0.51 g, 3.9 mmol), a catalytic amount of 4-dimethylaminopyridine and a solution of acetyl chloride (0.31 g, 3.9 mmol) in dichloromethane (5 ml) were added slowly to a solution of 5,6,7, 8-tetrahydro-8-hydroxy-6-((4-methoxyphenyl)methyl)-3-methylquinoline (1.12 g, 3.9 mmol) in dichloromethane (7 ml) at room temperature. The mixture was stirred overnight before further additions of acetyl chloride (0.32 g, 4 mmol) and diisopropylethylamine (0.51 g, 4 mnmol) were made. The mixture was again stirred overnight then diluted with dichloromethane (15 ml) and washed with water (1×15 ml), sodium hydrogen carbonate (1×15 ml), brine (1×15 ml) and water (1×15 ml). After drying (MgSO4) the reaction mixture was concentrated under reduced pressure to give an oil (1.46 g). This product was chromatographed on silica gel eluting with ethyl acetate/hexane (1:1) to give a fraction which on evaporation gave a solid (0.8 g). The solid was recrystallised from hexane to afford the title compound, (0.45 g), mp 113°-115° C., [α]D27 =+46° (1%CHCl3).

Provenance & Evidence