Hydrazine hydrate (1:1) → 1-amino-1,3-dihydrospiro[2H-indene-2,3'-[3H]indol]-2'(1'H)one

Participants

Reaction Steps

To a slurry consisting of 1,3-dihydro-1-[(phenylmethylene)amino]spiro[2H-indene-2,3'-[3H]indole]-2'(1'H)one (13.8 g), and absolute ethanol (300 ml) was added hydrazine hydrate (13.9 ml). The resulting mixture was heated at reflux for 3 hours, cooled to room temperature and the resulting precipitate removed by filtration. The mother liquor was concentrated and the resulting oil solidified upon addition of ethyl acetate-hexane. The resulting solid was recovered by filtration. Additional product was obtained from the mother liquor as above. Recrystallization from ethyl acetate afforded 1-amino- 1,3-dihydrospiro[2H-indene-2,3'-[3H]indol]-2'(1'H)one, m.p. 195°-197° C.

Provenance & Evidence