Diethyl Ether → 10-Methyl-9,10-dihydroacridine-9-carbonitrile

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Reaction Steps

A solution of 10.0 g (43.5 mmol) of acridine chloromethylate [A. Kaufmann et al, Ber. Dt. Chem. Ges. 42, 1999 (1909)] in 100 ml of water is covered with a layer of 200 ml of diethyl ether, and a solution of 3.13 g (48.0 mmol) of potassium cyanide in 20 ml of water is added. After about 30 minutes, the ether phase is separated off, the mixture is concentrated to 50 ml on a vacuum rotary evaporator and the product which has precipitated is filtered off. Crystallization of the crude product from ethanol gives 7.10 g (75%) of 9-cyano-9,10-dihydro-10-methyl-acridine, melting point 141°-143° C. (compound (106), Table 1).

Provenance & Evidence