Sodium Hydroxide → N-Ethyl-3,4-dimethoxy-6-methylphenanthren-9-amine

Participants

Reaction Steps

1700 ml (2.05M) of a 20% solution of diisobutylaluminium hydride in toluene are added at room temperature over a period of 45 minutes to a suspension of 105.7 g (0.342M) of 9-acetylamino-3,4-dimethoxy-6-methyl-phenanthrene in 1500 ml anhydrous tetrahydrofuran. The mixture is then warmed with stirring under a nitrogen atmosphere for 2 hours at 80°. The reaction mixture is then cooled at 0° and under nitrogen atmosphere and a mixture of 2500 ml 2N hydrochloric acid/ice, cooled at -10°, is added by portions at such a rate that the gas evolution is maintained. The acid solution is made alkaline to pH 10 by addition at 0° of 3 liters 2N sodium hydroxide and the mixture is extracted three times with methylene chloride/2-propanol 7:3. The organic phases are combined, washed, dried and evaporated to give the title compound. M.pt. 100°-102° after crystallisation from acetone/ether.

Provenance & Evidence