Hydrazine hydrate (1:1) → HCID 59018180, compound

Temperature

90 °C

The 4-(1-cyclopropanecarbonyl-2-cyclopropyl-2-oxo-ethoxy)-benzonitrile (44 g, 162 mmol) was dissolved in acetic acid (500 ml). A solution of hydrazine hydrate (8.7 ml, 179 mmol) in ethanol (50 ml) was then added at room temperature and the reaction mixture was heated to 90° C. for approximately 3 hours. The solvents were then evaporated under reduced pressure and the residues were partitioned between diethyl ether (600 ml) and dilute aqueous ammonium hydroxide (25 ml concentrated ammonium hydroxide in 500 ml water), and the layers were separated. The aqueous layer was further extracted with diethyl ether (3×200 ml) and the combined organic layers were washed with water (2×50 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure. The solid was slurried in diisopropyl ether (50 ml), filtered and rinsed with diisopropyl ether (2×30 ml) and pentane (2×100 ml) to provide the title compound (39.5 g, 58%) as a colourless solid. 1H-NMR (400 MHz, CDCl3): δ=0.76-0.81 (m, 8H), 1.59-1.65 (m, 2H), 7.01 (d, 2H), 7.60 (d, 2H); LRMS: APCl+: m/z 266 [MH+]; APCl−: m/z 264 [M−H]−.

1. customThe solvents were then evaporated under reduced pressure
2. customthe residues were partitioned between diethyl ether (600 ml) and dilute aqueous ammonium hydroxide (25 ml concentrated ammonium hydroxide in 500 ml water)
3. customthe layers were separated
4. extractionThe aqueous layer was further extracted with diethyl ether (3×200 ml)
5. washthe combined organic layers were washed with water (2×50 ml)
6. dry with materialdried over magnesium sulphate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. filtrationfiltered
10. washrinsed with diisopropyl ether (2×30 ml) and pentane (2×100 ml)

ORD record

ord-acb2a629ab7841728e264e0fa69ccde6

Source dataset

uspto-grants-2007_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07309712B2