Hydrazine hydrate (1:1) → 1-amino-1,3-dihydrospiro[2H-indene-2,3'-[3H]indol]-2'(1'H)one
Reaction equation
C1(C=[N:8][CH:9]2[C:17]3([C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[NH:19][C:18]3=[O:26])[CH2:16][C:15]3[C:10]2=[CH:11][CH:12]=[CH:13][CH:14]=3)C=CC=CC=1.O.NN>C(O)C>[NH2:8][CH:9]1[C:17]2([C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][C:18]2=[O:26])[CH2:16][C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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.