Potassium Hydroxide → 5-Hydrazinyl-2-methylpyridine

Temperature

0 °C

5-Amino-2-methyl-pyridine (9.90 g, 91.6 mmol) was dissolved in 6 N HCl (100 mL), cooled to 0° C., and vigorously stirred throughout the procedure. Sodium nitrite (6.32 g, 91.6 mmol) was dissolved in water (50 mL), this solution was added to the reaction solution. After 30 min, tin (II) chloride dihydrate (52.0 g, 230 mmol) in 6 N HCl (100 mL) was added, and the reaction slurry was stirred at 0° C. for 3h. The pH was adjusted to pH 14 with 40% aqueous potassium hydroxide solution. EtOAc extractions (6×250 mL), drying the organics over solid magnesium sulfate, and concentration afforded 5-hydrazino-2-methyl-pyridine as a tan solid (8.0 g). This material was used directly without further purification.

1. additionthis solution was added to the reaction solution
2. stirringthe reaction slurry was stirred at 0° C. for 3h
3. extractionEtOAc extractions (6×250 mL)
4. customdrying the
5. concentrationorganics over solid magnesium sulfate, and concentration

ORD record

ord-03be9dbd7fb14889979ea4fab5c01508

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06525046B1