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

Temperature

90 °C

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.

1. temperatureThe reaction was heated
2. temperaturethe reaction was heated
3. temperatureat reflux overnight
4. temperaturethe mixture was heated
5. temperatureat refluxed for 4 hours
6. concentrationThe mixture was concentrated to a residue
7. dissolutiondissolved in n-BuOH (120 ml)
8. additionhydrazine monohydrate (40 ml) was added
9. temperatureThe mixture was heated
10. temperatureat reflux for 6 days
11. temperatureThe reaction was cooled
12. additiondiluted with water
13. extractionextracted with EtOAc
14. concentrationThe organics were concentrated to an oil that
15. dissolutionwas dissolved in CH2Cl2
16. customdecanted away from the solids
17. concentrationThe organics were concentrated
18. customdried on high vacuum overnight
19. customThe crude product (24.47 g) was triturated in water
20. filtrationthe solids filtered

ORD record

ord-4f89df490c25494982cdd25bfd0ca628

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08362037B2