Derivatives of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene and related compounds VII. Improved syntheses of 11-h-benzo[5, 6] cyclohepta-[1,2-c] pyridin-11-one

An improved synthesis of the title compound is described. The base catalyzed condensation of 4-methylnicotinonitrile with benzaldehyde resulted in the isolation of trans- 4 -styrylnicotin-amide ( 2a ) in high yield. Hydrolysis to the acid and heating the acid 3a with polyphosphoric acid (ppa) gave the title compound 1a in good yields. Even higher yields of 1a were obtained in the presence of catalytic quantities of selenium. Also described are two other syntheses of the title compound as well as the preparation of a series of compounds related to 2a (Table I).