Potassium Hydroxide → 1-Acridinol, 1,2,3,4-tetrahydro-9-(methylamino)-

Participants

Reaction Conditions

Reaction Steps

In 50ml of dry tetrahydrofuran was dissolved 8.00 g of 3,4-dihydro-9-(methylamino)acridin-1(2H)-one. The mechanically stirred solution was cooled to -10° C. under N2 and 32ml (1 eq) of 1.1 M LiAlH4 solution in ether was added over 5 minutes. The stirring was continued for 45 minutes after the addition, during which the reaction went to completion. The excess LiAlH4 was neutralized with 1ml of saturated NH4Cl and the resulting salts dissolved in - 30% potassium hydroxide solution. The tetra-hydrofuran solution was separated and evaporated to an oil which solidified upon trituration with 1:1 dichloromethane/hexanes.

Provenance & Evidence