Ammonium Chloride → 1-Acridinol, 1,2,3,4-tetrahydro-9-(((4-fluorophenyl)methyl)amino)-

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Reaction Steps

In 100 ml of dry THF was dissolved 3.00 g of 3,4-dihydro-9-(4-fluorobenzyl)aminoacridin-1(2H)-one. The mechanically stirred solution was cooled in ice and 4.68 ml of 1M LiAlH4 in THF was added over 5 minutes. After 1/2 hour the reaction was complete by TLC. The excess hydride was neutralized with 1 ml of saturated ammonium chloride solution and the resulting salts were filtered. The THF filtrate was evaporated to a solid which was recrystallized from 1:1 dichloromethane/pentane to yield 2.47 g of solid, mp 169.5°-170° C.

Provenance & Evidence