Triethylamine → HCID 14098128, compound

Participants

Reaction Steps

To a solution of ethyl 2-oxoadamantane-1-carboxylate (5) (1.0 g, 4.5 mmol) and 3-chlorophenylhydrazine hydrochloride (3.6 g, 20 mmol) in 40 ml of ethanol is added triethylamine (2.0 g, 20 mmol). The reaction mixture is stirred at room temperature under a nitrogen atmosphere for 20 hours, then heated to reflux for 2 hours. After cooling to ambient temperature, the solvent is removed under reduced pressure and the crude residue solid is dissolved in 30 ml of methylene chloride. The organic extract is washed with 25 ml of diluted hydrochloric acid to remove the excess of 3-chlorophenylhydrazine, then dried over anhydrous magnesium sulfate. The solvent is evaporated to leave the title compound (6) as a dark-colored, viscous oil which is flash-chromatographed on silica gel using ether-pentane (2:8) as the eluent. Subsequent recrystallization from methanol provides the pure product as pale yellow needles melting at 119.5°-120.5° C. Anal. Calcd for C17H17ClN2O: C, 67.88; H, 5.70; N, 9:31; Cl, 11.79. Found: C, 67.54; H, 5.75; N, 9.12; Cl, 11.86.

Provenance & Evidence