Hydrazine hydrate (1:1) → 2-Hydrazinyl-6-methylpyridine

A mixture of 2-chloro-6-methylpyridine (50.6 g, 397 mmol) and hydrazine hydrate (80 mL, 1.65 mol) was heated under reflux for 20 hours. The reaction solution was allowed to cool to room temperature, and excess hydrazine hydrate was evaporated under reduced pressure, and the residue was poured into water. The solution was made basic by the addition of a sodium hydroxide solution, and the organic matter was extracted with chloroform. The extract was washed with saturated brine and water, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue thus obtained was chilled to crystallize, and the resulting crystals were washed with petroleum ether to give the title compound (31.0 g, 63% yield).

1. temperaturewas heated
2. temperatureunder reflux for 20 hours
3. customexcess hydrazine hydrate was evaporated under reduced pressure
4. additionthe residue was poured into water
5. additionThe solution was made basic by the addition of a sodium hydroxide solution
6. extractionthe organic matter was extracted with chloroform
7. washThe extract was washed with saturated brine and water
8. dry with materialdried over anhydrous magnesium sulfate
9. customthe solvent was evaporated under reduced pressure
10. customThe residue thus obtained
11. temperaturewas chilled
12. customto crystallize
13. washthe resulting crystals were washed with petroleum ether

ORD record

ord-699191f784344183841dba047a68b569

Source dataset

uspto-grants-2005_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06949648B2