Potassium Hydroxide → 5-Hydrazinyl-2-methoxypyridine

Temperature

0 °C

5-Amino-2-methoxypyridine (5.0 g, 40 mmol) was dissolved in 6 N HCl (10 mL), cooled to 0° C., and vigorously stirred throughout the procedure. Sodium nitrite (2.8 g, 41 mmol) was dissolved in water (10 mL) and this solution was added to the reaction solution. After 30 min, tin (II) chloride dihydrate (52 g, 230 mmol) in 6 N HCl (20 mL) was added, and the reaction slurry was stirred at 0° C. for 2.5 h. The pH was adjusted to 13 with 40% aqueous potassium hydroxide solution. Ethyl ether was added and the mixture was extracted with EtOAc (4×70 mL), dried (MgSO4) and concentrated to give 5-hydrazino-2-methoxypyridine as an orange solid (5.1 g).

1. additionthis solution was added to the reaction solution
2. stirringthe reaction slurry was stirred at 0° C. for 2.5 h
3. extractionthe mixture was extracted with EtOAc (4×70 mL)
4. dry with materialdried (MgSO4)
5. concentrationconcentrated

ORD record

ord-1eba747551e84b82be1000b2d968109d

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06660732B2