Hydrazine hydrate (1:1) → HCID 135508237, compound

To a mixture of (4E)-1-(6-hydroxy-1-benzofuran-2-yl)-5-phenylpent-4-ene-1,3-dione (0.48 mmol) and hydrazine monohydrate (0.02 g, 0.48 mmol) were added ethanol (24 mL) and acetic acid (1 drop) in a sealed tube. The reaction was heated at 65-700° C. overnight. The solvent was removed under reduced pressure to afford crude product. The crude product was purified by reverse phase HPLC. The fractions from HPLC were combined, neutralized with 1.0 N aqueous sodium hydroxide solution, and diluted with ethyl acetate (200 mL). The organic layer was washed with saturated aqueous sodium chloride (50 mL), dried over magnesium sulfate, filtered, and concentrated to afford the product (11% yield): 1H NMR (400 MHz, CD3Cl): δ 7.58 (br d, 2H), 7.35 (m, 4H), 7.25 (t, 2H), 7.10 (br d, 1H), 7.05 (br s, 1H), 6.94 (br d, 1H), 6.88 (br s, 1H), 6.75 (dd, 1H); MS (EI) for C19H14N2O2: 303 (MH+).

1. customThe solvent was removed under reduced pressure
2. customto afford crude product
3. customThe crude product was purified by reverse phase HPLC
4. additiondiluted with ethyl acetate (200 mL)
5. washThe organic layer was washed with saturated aqueous sodium chloride (50 mL)
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-7bbf47c5a6664d69a9c4302ca29e6e87

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08710038B2