Cesium carbonate → HCID 57532176, compound

Temperature

60 °C

A mixture of commercially available 3-chloro-2,4-pentanedione (1.2 ml, 10 mmol), 4-cyanophenol (1.19 g, 10 mmol), caesium carbonate (3.25 g, 10 mmol) and acetone (50 ml) was heated at 60° C. for 4 hours. After cooling, the reaction mixture was concentrated under reduced pressure. The resulting oil was diluted with dichloromethane (25 ml) and washed with 1M hydrochloric acid (30 ml). The aqueous layer, at pH 1, was extracted with dichloromethane (20 ml). The combined organic extracts were washed with brine, dried over magnesium sulphate, filtered and concentrated under reduced pressure to provide 4-(1-acetyl-2-oxopropoxy)benzonitrile (2.06 g, 9.4 mmol) which was used crude in the next step. 2-Hydroxyethyl hydrazine (169 μL, 2.5 mmol) was added to a stirred solution of a portion of the crude 4-(1-acetyl-2-oxopropoxy)benzonitrile (500 mg, 2.3 mmol) in acetic acid (5 ml) at room temperature under nitrogen, and the mixture was stirred at room temperature for 5 hours. Water (20 ml) was then added, and a solid triturated out and filtered off. This was recrystallised from ethyl acetate to provide the title compound (154 mg, 6%).

1. temperatureAfter cooling
2. concentrationthe reaction mixture was concentrated under reduced pressure
3. additionThe resulting oil was diluted with dichloromethane (25 ml)
4. washwashed with 1M hydrochloric acid (30 ml)
5. extractionThe aqueous layer, at pH 1, was extracted with dichloromethane (20 ml)
6. washThe combined organic extracts were washed with brine
7. dry with materialdried over magnesium sulphate
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure

ORD record

ord-67bc6811f48441788d347b9b8d4bc810

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07482375B2