Hydrochloric Acid → HCID 178525701, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of cis/trans-4-(3-amino-pyridin-2-yl)-cyclohexanecarboxylic acid ethyl ester (1:11) (0.570 g, 2.30 mmol) in concentrated hydrochloric acid (37%; 20 ml) was added sodium nitrite (0.292 g, 4.23 mmol) in small portions at 0-5° C. Stirring for 20 minutes was followed by addition of copper (I) chloride (0.493 g, 4.83 mmol) in one portion. After 10 minutes the reaction mixture was heated to 65° C. (oil bath temperature). The temperature was maintained at 65° C. for 20 h. The reaction mixture was cooled to 0-5° C. and adjusted to pH 4 by addition of aqueous sodium hydroxide solution (32%; 20 ml). The green aqueous layer was extracted with three 75 ml-portions of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography over SiO2 with n-heptane/ethyl acetate as eluent to give the title compound (0.424 g, 77%) as off-white solid. MS m/e: 240 ([M+H]+)

Provenance & Evidence