Hydrazine hydrate (1:1) → 1,10-Phenanthrolin-5-amine

Participants

Reaction Conditions

Reaction Steps

This compound was synthesized by the reduction of 5-nitro-1,10-phenanthroline. The procedure was manipulated under argon. To a suspension of 5-nitro-1,10-phenanthroline (2.06 g, 9.0 mmol) and 10% Pd/C (0.280 g) in 90 ml of 95% EtOH, hydrazine hydrate (2.0 ml, 42 mmol) was added dropwise. The mixture was heated for 3 h at 70° C. and then filtered hot through a glass-fiber filter to remove the catalyst. The yellow solution was concentrated to 25 ml and left at 4° C. for 24 hours. The precipitate was filtered off, washed with cold Et2O, and dried under vacuum for 24 hours to give 1.425 g of product (81%). 1H-NMR (DMSO-d6): δ=9.08 (m, 1H), 8.71 (m, 2H), 8.06 (m, 1H), 7.75 (q, 1H), 7.52 (q, 1H), 6.90 (s, 1H), 6.17 ppm (d, NH2). 13C-NMR (DMSO-d6): δ=149.3, 146.2, 144.8, 142.7, 140.5, 132.7, 130.8, 123.2, 122.0, 101.8 ppm.

Provenance & Evidence