2-hydrazino-4-methylpyridine hydrochloride synthesis

Yield:117879-50-2 44%

Reaction Conditions:

with hydrazine hydrate in 1,4-dioxane;methanol;

Steps:

S.4.1 (1)

(1) Synthesis of 2-hydrazino-4-methylpyridine hydrochloride In a 25 mL recovery flask, hydrazine hydrate (5 g) was added, and then 2-chloro-4-methylpyridine (1.0 g, 7.84 mmol) was slowly added thereto at room temperature while stirring. After refluxing for three hours, the reaction mixture was cooled and extracted with chloroformtwice. The organic phase was washed with saturated brine once and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off to give 2-hydrazino-4-methylpyridine(crude product). The crude product thus obtained was dissolved in methanol (2 mL), and 3 mL of 4N hydrochloride solution in dioxane was added thereto while stirring with cooling at 0°C. The solid precipitated out after stirring for 30 minutes at 0°C was collected by filtration and crystallized from a mixed solvent of methanol, chloroform, and hexane to give 0.55 g of 2-hydrazino-4-methylpyridinehydrochloride (yield 44%).

References:

EP2250998,2010,A1