Acridan → 10-[1-(2-Pyrrolin-2YL)-2-pyrrolin-2-YL]acridan

Participants

Reaction Steps

A mixture of acridan (3.6 g., 0.02 mole) and 2-chloro-1-(1-pyrrolin-2-yl) 2-pyrroline hydrochloride (5.1 g., 0.025 mole), obtained according to the method of H. Brederick, et al., Chem. Ber., 94, 2292 (1961), in 50 ml. of 1,2-dichloroethane is refluxed for a period of 15 hr. The mixture is sequentially extracted with 50 ml. of 1.5N hydrochloric acid and three 50 ml. portions of water. The combined acid-water extracts are basified with 5N potassium hydroxide, extracted with ether and the ethereal extract concentrated. Crystallization of the residue thus obtained from ethanol affords the free base 10-[1-(2-PYRROLIN-2YL)-2-PYRROLIN-2-YL]ACRIDAN, m.p. 179°-181° C. which is converted according to the procedure of Example 1 to 10-[1-(2-PYRROLIN-2-YL)-2-PYRROLIN-2-YL]ACIDAN HYDROCHLORIDE, m.p. 212.5°-216.5° C. (dec.) (corr.)., from ethanol-ether.

Provenance & Evidence