Potassium Hydroxide → Velnacrine

Participants

Reaction Conditions

Reaction Steps

In 100 ml of dry tetrahydrofuran was added 5.00 g of 9-amino-3,4-dihydroacridin-1(2H)-one. The mechanically stirred suspension was cooled to -5° C. and 21.41 ml (1.0 eq) of 1.1M LiAlH4 solution in ether was added dropwise. After completion of the addition, the reaction mixture was stirred for 2 hours, whereupon the reaction appeared complete based on thin layer chromatography analysis. The LiAlH4 was neutralized with 2 ml of saturated NH4Cl and the salts were dissolved with 30% potassium hydroxide. The insoluble product was filtered off and rinsed with water. The precipitate was then dissolved in 3N HCl and the residual insoluble salts filtered off. The acid solution was washed with EtOAc and made basic (pH 9) with 10% NaOH. The precipitated product was filtered and washed with water. After drying at 80° C. under vacuum overnight, 4.15 g (82%) of a powder was obtained, melting point 245° C.

Provenance & Evidence