Sodium Chloride → Isoquinoline-4-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium in n-hexane (90 ml, 2.4 M) was added at room temperature to a mixture of 500 ml of anhydrous ether and 500 ml of tetrahydrofuran under nitrogen. The solution was cooled to -68° C. and there was added 20.8 g of 4-bromoisoquinoline portionwise over a period of 30 minutes while maintaining the temperature at about -67° C. When addition was complete, the dark brown solution was stirred at -68° C. for 30 minutes. Then, a solution of 73 g of dimethylformamide in 150 ml of tetrahydrofuran at -68° C. was added all at once. The temperature rose to -57° C. and the reaction turned lighter brown. The mixture was stirred in dry ice for 15 minutes and then 100 ml of chilled ethanol was added over a period of 5 minutes. This was followed by the addition of 100 ml of saturated ammonium chloride solution and then 100 ml of saturated aqueous sodium chloride solution. The solution was then warmed to room temperature, the layers separated and the aqueous layer was washed once with ether. The organic layers were combined and dried over sodium sulfate and the solvent was evaporated. The resulting orange-brown oil was then dried. The residue was recrystallized from ethanol to give 4-isoquinolinecarboxaldehyde melting at about 104°-105° C.

Provenance & Evidence