Phenylhydrazine → HCID 178469890, compound

Participants

Reaction Steps

A mixture of diethyl 4-chloro-3,5-pyridinedicarboxylate (3.09 g, 12.0 mmol) and phenylhydrazine (1.42 ml, 14.4 mmol) in ethanol (100 ml) was degassed by evaporating under vacuum and refilling with nitrogen several times. The mixture was then stirred at reflux for 17 h under nitrogen. The mixture was left to cool in the fridge for a few hours, then filtered from a solid, which was washed with ethanol and ethyl acetate. The combined filtrates were evaporated in vacuo, and the residue was purified by flash chromatography (silica gel, 5% MeOH/CH2Cl2) to afford 1.559 g (46%) as an orange solid; 1H NMR (360 MHz, DMSO-d6) δ1.35 (3H t, J 7.1 Hz), 4.34 (2H, q, J 7.1 Hz), 7.18 (1H, t, J 7.3 Hz), 7.44 (2H, t, J 7.5 Hz), 8.14 (1H, s), 8.19 (2H, d, J 7.6 Hz), 8.57 (1H, s), 12.49 (1H, br s).

Provenance & Evidence