Ammonium Chloride → 104675-50-5

Participants

Reaction Steps

In 75ml of dry tetrahydrofuran was dissolved 2.45 g of 9-phenethylamino-3,4-dihydroacridin-1(2H)-one. The solution was cooled in ice and 7.0ml (1 eq) of 1.1 M LiAlH4 in Et2O was added dropwise. After 0.5 hour the reaction was complete. It was neutralized with 0.5ml saturated NH4Cl solution and the resulting inorganic salts were filtered off. The filterate was evaporated to a solid and the maleate salt was found by adding a solution of 1.1 eq maleic acid in isopropanol to a suspension of the product in isopropanol. A solution formed initially but the salt precipitated out over 0.5 hour at ambient temperatures. The salt was filtered off and recrystallized from 5:1 EtOAc/MeOH and dried at 80° C. in vacuo to yield 1.14 g (32%) of a solid, melting point 169° C.

Provenance & Evidence