Hydrazine hydrate (1:1) → HCID 66643279, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 2A (10 g, 41 mmol) in EtOH (85 mL) was added hydrazine hydrate (3.0 mL, 62 mmol). This mixture was warmed to reflux (85° C.) and was allowed to stir for 20 hours. The mixture was cooled to ambient temperature then 4,4-dimethyl-3-oxopentanenitrile (7.8 g, 61.9 mmol) was added and the mixture was again warmed to reflux (85° C.) and was allowed to stir for 4 hours. The mixture was concentrated under reduced pressure and the residue was dissolved in CH2Cl2 (50 mL) and saturated aqueous NaHCO3 (50 mL) was added. The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×10 mL). The combined organics were dried over Na2SO4, filtered, concentrated under reduced pressure and purified via column chromatography (SiO2, 50% hexanes/EtOAc) to provide the title compound (7.6 g, 36.3 mmol, 88% yield). MS (DCI/NH3) m/z 210 (M+H)+.

Provenance & Evidence