2-Aminofluorene → HCID 66626347, compound

Participants

Reaction Steps

2-Thiophenecarboxaldehyde (80.4 mg, 0.72 mmol) was added to 2-aminofluorene (100 mg, 0.55 mmol) and refluxed in isopropanol for 12 hours with a catalytic amount of TFA. The solvent was evaporated and the product was purified by flash chromatography using anhydrous basic activated alumina gel (AlO2) and 40% ethyl acetate and 60% hexanes. The title compound was obtained as a yellow product. (45.4 mg, 0.165 mmol, 30%). M.p.: 143° C. 1H-NMR (300 MHz, [D] DMSO): δ=8.65 (s, 1H), 7.89 (t, 2H, 3J=10.9 Hz), 7.81 (d, 1H, 3J=6.7 Hz), 7.69 (dd, 1H, 3J=4.8 Hz, 4J=1.4 Hz), 7.57 (d, 1H, 3J=9.76 Hz), 7.50 (s, 1H), 7.37 (t, 1H, 3J=9.88 Hz), 7.32 (t, 2H, 3J=11 Hz), 7.22 (dd, 1H, 3J=4.84 Hz, 4J=1.8 Hz), 3.94 (s, 2H). 13C-NMR (300 MHz, [D] DMSO): δ=152.9, 148.4, 144.2, 143.1, 144.4, 141.0, 129.7, 128.8, 128.2, 128.4, 127.4, 127.1, 126.8, 125.8, 123.6, 120.3, 36.5. C.V. −1.36, −0.96, −0.56, −0.02, 0.62, 1.39 V. In 0.1 M TBAPF6 as supporting electrolyte in degassed anhydrous acetonitrile λmax=352 nm. λem=302 nm. Eg=454 nm, 62.95 Kcal/mol. ΔE=300 nm, 95.26 Kcal/mol.

Provenance & Evidence