Hydrazine hydrate (1:1) → 3-(6-Hydrazinyl-3-pyridazinyl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(6-chloro-pyridazin-3-yl)-benzonitrile (75.6 g, 350 mmol) in 900 mL of dried pyridine was cooled in an ice bath and 119.2 mL of hydrazine hydrate was added. The cooling was continued so as to keep the temperature below 30° C. at which time yellow needle separated. The mixture was then heated to 65° C. and stirred overnight. Then the mixture was concentrated and the residue was washed with water and Methanol to return the title compound (60 g, 81%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6): δ 8.38˜8.39 (m, 1H), 8.32˜8.35 (m, 1H), 8.24 (s, 1H), 7.97˜8.00 (d, 1H), 7.82˜7.85 (m, 1H), 7.64˜7.69 (m, 1H), 7.09˜7.12 (d, 1H), 4.39 (s, 2H); MS (m/z) 212.1 [M++1].

Provenance & Evidence