Methylhydrazine → Pyridine, 2-(1-methylhydrazinyl)-

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Reaction Steps

2-Bromopyridine (5 mL, 52.4 mmol) and methylhydrazine (20 mL, 360 mmol) were mixed together in a flask fitted with a water-condenser. After a few minutes a vigorous exothermic reaction occurred with refluxing of the methylhydrazine. When the reaction had subsided, the mixture was left for 16 hours, and the excess methylhydrazine was removed under reduced pressure. The cooled residue was stirred with aqueous sodium hydroxide solution (30 ml of 20%), and the resulting solution was extracted with ether (3×100 ml). The combined extracts were dried (K2CO3) and purified by silica gel chromatography 0-3% EtOH/CH2Cl2 to give 4.8 g of N-Methyl-N-pyridin-2-yl-hydrazine.

Provenance & Evidence