13C-13C spin-spin coupling constants in six-membered ring azaaromatic compounds

✍ Scribed by A. Yu. Denisov; V. I. Mamatyuk; O. P. Shkurko

• Publisher: Springer US
• Year: 1988
• Tongue: English
• Weight: 602 KB
• Volume: 24
• Category: Article
• ISSN: 0009-3122
• DOI: 10.1007/bf00474049

✦ Synopsis

3'-Amino-spiro-[4-azafluorene-9~l'-indane] (IX). A solution of 0.18 g (0.6 mmole) oxime VIII and i ml hydrazine hydrate in i0 ml ethanol Was stirred for 72 h in the presence of a catalytic quantity of Raney nickel. After the catalyst was removed 20 ml water was added to the solution and the precipitate was removed by filtration. Yield 0.12 g (70.6%) of amine IX, mp 202-204~ (from heptane). IR spectrum: 3365 cm -I (NH=). Found, %: N 9.6, M + 284. C=0HI6N 2. Calculated, %: N 9.9, M 284.

3'-Acetylamino-spiro-[4-azafluorene-9~l'-indane] (X). A mixture of 0.05 g (0.18 mmole) amine IX and 5 ml acetic anhydride was heated for 20 min at 60~

The reaction mixture was poured into water (20 ml) and neutralized with sodium bicarbonate, the precipitate was filtered and washed with 30 ml water and 5 ml ether and then dried over phosphorus pentoxide. Yield 0.025 g (44%), mp 277-279~ IR spectrum: 3210, 3110 (NH), 1685 cm -I (CO).