Ammonium Chloride → 1-Acridinol, 1,2,3,4-tetrahydro-9-(methylamino)-

Participants

Reaction Conditions

Reaction Steps

In 50 ml 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 32 ml (1 eq) of 1.1M 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 1 ml of saturated NH4Cl and the resulting salts dissolved in 30% potassium hydroxide solution. The tetrahydrofuran solution was separated and evaporated to an oil which solidified upon trituration with 1:1 dichloromethane/hexanes. The solid was recrystallized from 10:1 hexanes/tetrahydrofuran to yield 5.89 g (73%) of a solid, melting point 160°-161° C. ANALYSIS: Calculated for C14H16N2O: 73.65% C, 7.06% H, 12.27% N. Found: 73.61% C, 7.00% H, 12.39% N.

Provenance & Evidence