Tetrahydrofuran → 7,8-Dihydro-6H-isoquinolin-5-one oxime

Participants

Reaction Steps

In a nitrogen atmosphere, tetrahydrofuran (125 mL) solution of 6.5 mL of 5,6,7,8-tetrahydroisoquinoline was added to tetrahydrofuran (100 mL) solution of 11.4 g of potassium tert-butoxide, and stirred at room temperature for 18 hours. Next, 17.5 mL of tert-butyl nitrite was dropwise added to the reaction liquid at 0° C., and stirred at room temperature for 18 hours. Saturated saline water was added to the reaction liquid, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was crystallized from water/ethanol to obtain 6.06 g of the entitled compound as a pale brown solid.

Provenance & Evidence