Pyridine → HCID 178472333, compound

Participants

Reaction Steps

Batch 1: To a solution of trans-4-(6-amino-pyridin-2-yl)-cyclohexanecarboxylic acid ethyl ester (0.050 g, 0.20 mmol) in 70% hydrogen fluoride in pyridine (0.47 ml, 18 mmol) was added solid sodium nitrite (0.015 g, 0.22 mmol) at 0-5° C. The cooling bath was removed after 20 minutes and the reaction mixture was stirred for 30 minutes at room temperature. The reaction mixture was partitioned between an ice-water mixture (50 ml) and tert-butyl methyl ether (50 ml). The organic layer was collected. The aqueous layer was extracted with two 50-ml portions of tert-butyl methyl ether. The combined organic layers were washed with one 30-ml portion of 2M aqueous sodium hydroxide solution and one 30-ml portion of brine, dried over anhydrous sodium sulfate and concentrated to dryness to give the crude title compound (0.08 g).

Provenance & Evidence