Sodium Hydroxide → HCID 136352217, compound

Participants

Reaction Conditions

Reaction Steps

To an ice cooled solution of 2-isoquinolin-3-yl-chromen-4-one O-tert-butyl-oxime (136 mg, 0.39 mmol) in dichloromethane (10 ml) was cautiously added dropwise a 1M solution of titanium tetrachloride in dichloromethane (1.2 ml, 1.2 mmol). The mixture was stirred at 0° C. 2 hours, then at room temperature 2 more hours and poured onto ice cold water (100 ml). The mixture was basified using a 6N aqueous sodium hydroxide solution until pH 10 and the yellow precipitate was collected by filtration. The solid was washed with water, dried and purified by flash chromatography (cyclohexane/ethyl acetate/dichloromethane:80/10/10; 60/30/10 then 0/50/50) to yield 2-isoquinolin-3-yl-chromen-4-one oxime (71 mg, 62%) as a yellow solid. The product was isolated as a 95/5 mixture of Z/E oxime isomers.

Provenance & Evidence