Hydrazine → 2-Hydrazinyl-4-(2-methoxyethoxy)pyridine

Participants

Reaction Steps

Hydrazine (10 mL, 318.6 mmol) was added to a solution of 2-chloro-4-(2-methoxyethoxy)pyridine (1.00 g, 5.330 mmol) in pyridine (25 mL). The reaction was heated to reflux. After 18 hours the reaction mixture was partitioned between H2O and DCM and the aqueous phase was extracted with DCM. The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified via flash column chromatography (40:1 DCM/MeOH followed by 20:1 DCM/MeOH) to provide 320 mg (33%) of desired product as a white solid.

Provenance & Evidence