6-Methoxyquinoline → Quinoline, 1,2,3,4-tetrahydro-6-methoxy-

Participants

Reaction Conditions

Reaction Steps

Based on G. W. Gribble, et al., Synthesis, 1975, 650-652, 6-methoxyquinoline (1.26 g, 7.9 mmol) was dissolved in glacial acetic acid (20 mL) under N2 at RT. Solid NaCNBH3 (2 g, 32 mmol) was added in small portions over a 45 min period. The reaction was heated to 50° C. for 8 h, then cooled to RT and stirred overnight. The reaction was quenched by cooling it to 0° C., and the pH of the solution was adjusted to 14 with 2 N NaOH. The solution was extracted 3 times with EtOAc. The EtOAc extracts were washed brine, combined, dried over Na2SO4, filtered, and concentrated, then eluted through a 17×2.5 cm column of silica gel (5% and 10% EtOAc/Hexane step gradient) giving 6-methoxy-1,2,3,4-tetrahydroquinoline as a red oil. This material was used without further purification.

Provenance & Evidence