Hydrazine → HCID 21702028, compound

A mixture of 3′-methoxyacetophenone (1.5 g, 10 m mol), anhydrous hydrazine (1.28 g, 40 m mol) and dry ethanol (10 ml) was heated under reflux for 3 hours. Thereafter, the solvent was distilled off under reduced pressure. The residue was subjected to chromatography on silica gel (50 g) using ethyl acetate-hexane (1:1), and eluted with ethyl acetate-hexane (1:1) and then with ethyl acetate. The resulting yellow oily material (1.2 g) was dissolved in ethanol (20 ml). After the addition of 5% palladium-carbon (0.5 g), this solution was stirred in an atmosphere of hydrogen (40 kg/cm2) for 48 hours. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to chromatography on silica gel (30 g) using chloroform-methanol (100:1), and eluted with chloroform-methanol (100:1) and then with chloroformmethanol (10:1). Thus, the desired compound (0.68 g, 41%) was obtained as an oily material.

1. temperaturewas heated
2. temperatureunder reflux for 3 hours
3. distillationThereafter, the solvent was distilled off under reduced pressure
4. washeluted with ethyl acetate-hexane (1:1)
5. dissolutionThe resulting yellow oily material (1.2 g) was dissolved in ethanol (20 ml)
6. additionAfter the addition of 5% palladium-carbon (0.5 g)
7. filtrationThe catalyst was filtered off
8. concentrationthe filtrate was concentrated under reduced pressure
9. washeluted with chloroform-methanol (100:1)

ORD record

ord-04c89f9c3b7b4519b4ecd026d5acded1

Source dataset

uspto-grants-2001_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06291485B1