Sodium Hydroxide → HCID 14293583, compound

Participants

Reaction Steps

A solution of 2-cyclohexylquinoline (2.66 g, 12.61 mmol) in glacial acetic acid (25 ml) was treated with sodium cyanoborohydride (2.38 g, 37.82 mmol) and stirred at room temperature for 4 h and then 40° C. for 18 h. The mixture was then treated with 2 M sodium hydroxide (200 ml), stirred for 30 min and extracted into ethyl acetate (3×100 ml). The combined organic layers were then washed with water (3×100 ml), dried with sodium sulfate, evaporated under reduced pressure and the residue purified by flash chromatography eluting with 0-3% (v/v) ethyl acetate in isohexane to afford 2-cyclohexyl-1,2,3,4-tetrahydroquinoline as a yellow oil (1.61 g, 7.49 mmol).

Provenance & Evidence