Hydrochloric Acid → HCID 178472337, compound

Participants

Reaction Steps

To a solution of cis/trans-4-(4-amino-pyridin-2-yl)-cyclohexanecarboxylic acid ethyl ester (1:9) (0.638 g, 2.57 mmol) in concentrated hydrochloric acid (11.0 ml, 128 mmol) was added in small portions sodium nitrite (4.43 g, 64.2 mmol) at 0-5° C. The reaction mixture was allowed to warm to room temperature. Copper (I) chloride (10.7 g, 108 mmol) was added in one portion. Stirring for 2 h was followed by quenching with 32% sodium hydroxide solution (9.52 ml, 103 mmol) at 0-5° C. The reaction mixture was partitioned between dichloromethane (50 ml) and water (20 ml). The layers were separated. The aqueous layer was extracted with two 100 ml-portions of dichloromethane. The combined organic layers were washed with one 25 ml-portion of water, dried over anhydrous sodium sulfate and concentrated in vacuo. Flash-chromatography with n-heptane/ethyl acetate as eluent gave the title compound (0.186 g, 27%) as colorless oil.

Provenance & Evidence