Potassium Carbonate → 3-(Benzyloxy)-2-hydrazinopyridine

Participants

Reaction Conditions

Reaction Steps

3-(Benzyloxy)-2-chloropyridine (22.3 g, 101 mmol) was dissolved in EtOH (300 ml) and hydrazine monohydrate (10.2 ml, 203 mmol) added. The reaction was heated to reflux at 90° C. for 90 minutes. Hydrazine monohydrate (50 ml) was added and the reaction was heated at reflux overnight. K2CO3 (10 g) was added and the mixture was heated at refluxed for 4 hours. The mixture was concentrated to a residue and dissolved in n-BuOH (120 ml) and hydrazine monohydrate (40 ml) was added. The mixture was heated at reflux for 6 days. The reaction was cooled, diluted with water and extracted with EtOAc. The organics were concentrated to an oil that was dissolved in CH2Cl2 and decanted away from the solids. The organics were concentrated and dried on high vacuum overnight. The residue solidified on high vacuum. The crude product (24.47 g) was triturated in water and the solids filtered to give 3-(benzyloxy)-2-hydrazinylpyridine (14.9 g, 68% yield) as a solid.

Provenance & Evidence