Sodium borohydride → HCID 68182333, compound

Participants

Reaction Steps

To a stirred solution of 6-methyl-2-(methylamino)quinoline-3-carbaldehyde MDE 32036 (134 mg, 0.67 mmol) in THF (10 mL) at 0° C. in a 50 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (25 mg, 0.66 mmol) and the mixture was stirred overnight at RT then cooled in an ice bath before quenching by addition of a 6 N aq. HCl solution (0.45 mL). After stirring for 15 min at +4° C., the mixture was basified with a 2 N aq. NaOH solution (1.35 mL). THF was then removed at 40° C. under vacuum and the solution was extracted with CH2Cl2 (50 mL), washed with brine (10 mL), dried over Na2SO4, filtered, and concentrated under vacuum. Purification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 50:50) provided, after evaporation and drying, 6-methyl-2-(methylamino)quinolin-3-yl)methanol MDE32060 as a white solid (73 mg, 55% yield).

Provenance & Evidence