Quinoline, 6-fluoro- → 6-Fluoro-1,2,3,4-tetrahydroquinoline

Participants

Reaction Steps

Sodium cyanoborohydride (6.45 g, 103 mmol) was added gradually to the solution of 6-fluoro quinoline (5 g, 34 mmol) in glacial acetic acid (100 ml) at ambient temperature. After stirring for 12 h the reaction mixture was quenched in water and extracted with EtOAc (3×50 mL). The combined organic layers were washed with water, brine and dried over sodium sulfate, filtered and evaporated in vacuo, the residue was purified by a silica gel column with 1% to 5% ethyl acetate in petroleum ether to afford 6-fluoro-1,2,3,4-tetrahydroquinoline as a light yellow liquid (3.65 g, 71.6%).

Provenance & Evidence