Hydrazine → HCID 68840209, compound

A solution of the product from Step 2 (3.60 g, 9.49 mmol) and anhydrous hydrazine (0.61 g, 19.0 mmol) in ethanol (36 mL) was heated at reflux temperature for 2 h. The reaction was cooled to room temperature and the precipitate was removed by filtration and washed with ethanol. The filtrate was concentrated to dryness and the residue was dissolved in EtOAc and washed with saturated sodium bicarbonate solution. The organic layer was then dried over sodium sulfate, filtered and concentrated to an oil that solidified upon standing to afford 2.20 g (93%) of the product as a white solid. 1H NMR (400 MHz, Chloroform-d) δ 7.36-7.22 (m, 5H), 5.12-5.00 (br s, 1H), 3.74-3.57 (m, 1H), 3.64 (s, 3H), 3.63-3.54 (m, 2H), 3.34-3.25 (m, 1H), 3.14-3.02 (m, 1H), 2.88-2.53 (m, 1H), 2.54-2.42 (m, 1H), 2.17-2.10 (m, 1H) 2.00-1.60 (br s, 2H). MS 250.3 (AP+, 100).

1. temperatureat reflux temperature for 2 h
2. customthe precipitate was removed by filtration
3. washwashed with ethanol
4. concentrationThe filtrate was concentrated to dryness
5. dissolutionthe residue was dissolved in EtOAc
6. washwashed with saturated sodium bicarbonate solution
7. dry with materialThe organic layer was then dried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated to an oil that

ORD record

ord-3c23e3ce234341b3b9cdbef2dd1c18d9

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07485641B2