Hydrochloric Acid → HCID 71253087, compound

Participants

Reaction Steps

To a solution of 4,4-dimethyl-3-oxopentanenitrile (754 mg, 6.02 mmol) and conc hydrochloric acid (12 M, 500 μL, 6.0 mmol) in EtOH (25 mL) was added 3,5-dimethoxyphenylhydrazine hydrochloride (1.12 g, 5.47 mmol) and the reaction mixture heated at reflux for 1 hr and then cooled to RT. After 23 hr the reaction mixture was diluted with saturated aq. NaHCO3 (50 mL) then extracted with DCM (4×50 mL). The combined organic extracts were dried and evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, 40 g, EtOAc in isohexane, 0-100%, gradient elution) and then by SCX capture and release to afford the title compound, Intermediate A25, as a dark orange solid (400 mg, 26%); Rt 1.70 min (Method 2); m/z 276 (M+H)+, (ES+).

Provenance & Evidence