1.68 g (4.27 mmole) of 9,9-bis(4-pyridinylmethyl)-2-nitrofluorene was suspended in 5 ml of ethanol/water (1:1) and 1.43 g of powdered iron was added. The mixture was heated to boiling and 0.3 ml conc. hydrochloric acid was added dropwise. After completion of addition, the mixture was refluxed 2 hrs. The cooled mixture was basified with KOH, iron hydroxide filtered off and the filtrate evaporated. The residue was dissolved in ether-CH2Cl2 (3:1), washed with water, saturated sodium chloride, dried (MgSO4) and evaporated to yield 1.28 g of the title product. NMR (CDCl3, 200 MHz) δ: 3.33(s,4H), 6.53(dd,4H), 6.60(d,J=2.0 Hz,1H), 6.79(d,J=2.0 Hz,1H), 7.18(d,4H), 7.37(dd,1H), 8.11(dd,4H), m.p. (trihydrochloride) >300°. HRMS calculated for C25H21N3 : 363.1735 Found: 363.1728.
